A short and efficient synthesis of unnatural ( R)-nicotine
A short and efficient synthesis of unnatural ( R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%)...
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| Published in | Tetrahedron letters Vol. 41; no. 48; pp. 9245 - 9249 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
25.11.2000
Elsevier |
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| Abstract | A short and efficient synthesis of unnatural (
R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). |
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| AbstractList | A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd. All rights reserved. A short and efficient synthesis of unnatural ( R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). |
| Author | Lebreton, Jacques Villiéras, Jean Girard, Sandrine Robins, Richard J |
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| CitedBy_id | crossref_primary_10_1002_chin_200108213 crossref_primary_10_1016_j_abb_2006_12_013 crossref_primary_10_1002_ciuz_200800464 crossref_primary_10_1016_j_tet_2007_04_100 crossref_primary_10_4236_ijoc_2022_124016 crossref_primary_10_1016_j_ejphar_2007_02_038 crossref_primary_10_1016_S0040_4020_02_00819_0 crossref_primary_10_1016_S0957_4166_02_00743_7 crossref_primary_10_1021_acs_orglett_1c00856 crossref_primary_10_1039_c3ra42821d crossref_primary_10_1002_slct_202104425 crossref_primary_10_1016_j_tetlet_2011_01_032 crossref_primary_10_1021_jo020501y crossref_primary_10_1021_ol5008235 crossref_primary_10_1016_S0168_9452_01_00509_X crossref_primary_10_1016_S0957_4166_01_00204_X crossref_primary_10_1002_ejoc_200300193 crossref_primary_10_1021_ja0605265 crossref_primary_10_1007_s00216_019_02023_6 crossref_primary_10_1039_C4OB00767K crossref_primary_10_1002_jlcr_1578 crossref_primary_10_1016_S0040_4039_01_00317_3 crossref_primary_10_1002_ejoc_200400670 crossref_primary_10_1016_j_tetasy_2005_05_026 |
| Cites_doi | 10.1021/jm00188a009 10.1007/BF02244748 10.1021/ja00312a062 10.1016/S0040-4020(98)00487-6 10.1021/jo9509723 10.1016/S0040-4039(99)01606-8 10.1021/jo00050a045 10.1016/S0040-4020(97)00802-8 10.1016/0028-3908(95)00034-4 10.1021/jo991609p 10.1055/s-1992-26174 10.1055/s-1997-1206 10.1021/jo00074a008 10.1021/jo00354a003 10.1021/cen-v078n013.p023 |
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| Issue | 48 |
| Keywords | asymmetric synthesis boron and compounds azides allylation alkaloids ALCOHOLS CHIRAL SYNTHESIS NICOTINIC ACETYLCHOLINE-RECEPTORS ORGANOBORANES |
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| References | 7847–7850. (b) Swango, J. H.; Bhatti, B. S.; Quershi, M. M.; Crooks, P. A. The combined extracts were dried over anhydrous MgSO 2.28 Hz, H Cl 1749; (c) Raatz, D.; Innertsberger, C.; Reiser, O. PrOH 95:5 v/v; flow rate: 0.5 ml/min; retention time 11.2 min for the 148.6; 148.0; 140.5; 134.0; 123.2; 60.0; 47.0; 34.5; 25.6. separation conditions by chiral HPLC were: Chiracel OD-H column (0.46×15 cm): elution with a mixture of hexane H NMR (200 MHz, CDCl C NMR (50 MHz, CDCl and 28.5 min for the Nybäck, Halldin, Ahlin, Curvall, Erikson (BIB7) 1994; 115 4169–4194. 6614–6617; Waid, P. P.; Flynn, G. A.; Huber, E. W.; Sabol, J. S. For the asymmetric synthesis of allyldiisopinocampheylborane from (−)-Ipc alcohol Removal of the solvent left an oil which was purified by bulb-to-bulb distillation yielding 290 mg (85%) of 7.70 (1H, pseudo dt nicotine 615; (c) Sankar, T. K.; Basak, S.; Ghosh, S. K. 4.88 Hz, H PrOH 95:5 v/v; flow rate: 0.5 ml/min; retention time 26 min for Galzi, Changeux (BIB1) 1995; 34 For similar problems of pyridine complex formation, see: (a) Hull, K. G.; Visnick, M.; Tautz, W.; Sheffron, A. To a stirred solution of 1.4 ml (13.9 mmol) of freshly distilled cyclohexene in 10 mL of THF at 0°C was added dropwise 3.5 ml (7 mmol) of 2.0 M BH For complex in THF. The resulting white suspension of dicyclohexylborane was stirred for 1 h at 0°C and then cooled to −15°C prior to the addition of 400 mg (2.3 mmol) of azide ) For a review of this field, see: Carboni, B.; Vaultier, M. , For the preparation of nornicotine 1069–1073. - 7.9 Hz . Alvarez, S. G.; Alvarez, M. T. and 34.0 min for the 2.06 Hz, H Uchi, J.; Takagi, T.; Ueno, T.; Hiraoka, T.; Yoemiitsu, O.; Tsukube, H. in 10 mL of THF. The resulting mixture was allowed to warm up to rt. After 12 h, the reaction was quenched with MeOH, diluted with ether and the organic layer was extracted with 1N aqueous HCl. The combined aqueous layers were treated with 30% aqueous NaOH solution until pH 13–14, and then extracted with CH 1.7 Hz, H 432–439. 7.22 (1H, dd 2 Hz, H Representative procedure for Thompson, Humphrey, DeMarco, Mathre, Grabowski (BIB20) 1993; 58 BCl (purchased from Aldrich Chemical Co.) see: Jadhav, P. K.; Bhat, K. S.; Perumal, T.; Brown, H. C. 41–44. Bleicher, Cosford, Herbaut, McCallum, McDonald (BIB9) 1998; 63 3.1 (2H, m, H 861; (b) Che, D.; Siegl, J.; Seitz, G. 4091–4094. 8952. nornicotine), see: (a) Loh, T.-P.; Zhou, J.-R.; Li, X.-R.; Sim, K.-Y. nicotine (or 2.2 (1H, m, H 5299–5230. and 9.1 min for the Brennan (BIB2) 2000; 78 7.32 Hz SMe 461–467; (b) Holladay, M. W.; Dart, M. J.; Lynch, J. K. S-695. (d) Chavdarian, C. G.; Sanders, E. B.; Bassfield, R. L. 12405–12414; (b) Ling Ng, P.; Lambert, J. N. 759–762. PrOH 95:5 v/v; flow rate: 0.5 ml/min; retention time 7.8 min for 573; (a) Fürstner, A.; Thiel, O. R. PrOH 95:5 v/v; flow rate: 0.5 ml/min; retention time 29.1 min for homoallylic alcohol separation conditions were: Chiracel OD-H column (0.46×15 cm): elution with a mixture of hexane All enantiomeric excesses were determined by chiral HPLC. For Racherla, Liao, Brown (BIB14) 1992; 57 isomer. 413–414 and references cited therein. azide separation conditions by chiral HPLC: Chiracel OD-H column (0.46×15 cm): elution with a mixture of hexane Singh, V. K. 8.6 (1H, d 1003–1008 and references cited therein. For recent examples, see: (a) Salmon, A.; Carboni, B. 4.88 Hz (a) Wittenberger, S. J. Roush, Walts, Hoong (BIB11) 1985; 107 For recent examples, see: (a) Turner, S. C.; Zhai, H.; Rapoport, H. azide and 12.6 min for the 1.66 (1H, m, H 1907; (d) Willoughby, C. A.; Buchwald, S. L. For reviews in this field, see: (a) Lloyd, G. K.; Williams, M. 2.1 (1H, NH); 1.9 (2H, m, H Aceto, Martin, Uwaydah, May, Harris, Izazola-Conde, Deway, Bradshaw, Vincek (BIB6) 1979; 22 316–318. (c) Swango, J. H.; Quershi, M. M.; Crooks, P. A. 356–358. (b) Bleicher, L. S.; Cosford, N. D. P. 4.14 (1H 1738; (b) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Lutz, Graf, Knochel (BIB12) 1998; 54 605–617 and references cited therein. 8.45 (1H, dd RACHERLA, US (WOS:A1992JZ57900045) 1992; 57 Brennan, MB (WOS:000086124600038) 2000; 78 GALZI, JL (WOS:A1995RK06800001) 1995; 34 Furstner, A (WOS:000086020300018) 2000; 65 Salmon, A (WOS:000075989300007) 1998; 567 Alvarez, SG (WOS:A1997WY96100005) 1997 Che, DQ (WOS:000079213400019) 1999; 10 Hull, KG (WOS:A1997XV79400007) 1997; 53 NYBACK, H (WOS:A1994NR46400005) 1994; 115 Lloyd, GK (WOS:000084929700001) 2000; 292 ACETO, MD (WOS:A1979GF57700009) 1979; 22 Turner, SC (WOS:000085335200031) 2000; 65 Swango, J. (BCI:BCI199800105956) 1997; 14 SINGH, VK (WOS:A1992JD39400001) 1992 Raatz, D (WOS:000084823800013) 1999 ROUSH, WR (WOS:A1985AXB4600062) 1985; 107 SANKAR TK (WOS:000165482600010.24) 2000; 41 Wittenberger, SJ (WOS:A1996TQ14600054) 1996; 61 WILLOUGHBY, CA (WOS:A1994PK97900012) 1994; 116 Ng, PL (WOS:000084037100011) 1999 Loh, TP (WOS:000083043400033) 1999; 40 Bleicher, LS (WOS:000081474300045) 1999; 64 Bleicher, LS (WOS:000072215400034) 1998; 63 JADHAV, PK (WOS:A1986A261000003) 1986; 51 Lutz, C (WOS:000075312400008) 1998; 54 UCHI J (WOS:000165482600010.30) 1999 Holladay, MW (WOS:000071343300001) 1997; 40 CHAVDARIAN, CG (WOS:A1982NF10900034) 1982; 47 CARBONI, B (WOS:A1995TH54900001) 1995; 132 Cook, GR (WOS:000083701900021) 1999; 1 THOMPSON, AS (WOS:A1993MD98500008) 1993; 58 Waid, PP (WOS:A1996UP92300002) 1996; 37 Swango, JH (WOS:000079845000009) 1999; 11 10.1016/S0040-4039(00)01675-0_BIB17 10.1016/S0040-4039(00)01675-0_BIB16 10.1016/S0040-4039(00)01675-0_BIB15 Thompson (10.1016/S0040-4039(00)01675-0_BIB20) 1993; 58 10.1016/S0040-4039(00)01675-0_BIB19 10.1016/S0040-4039(00)01675-0_BIB18 Galzi (10.1016/S0040-4039(00)01675-0_BIB1) 1995; 34 Brennan (10.1016/S0040-4039(00)01675-0_BIB2) 2000; 78 Lutz (10.1016/S0040-4039(00)01675-0_BIB12) 1998; 54 10.1016/S0040-4039(00)01675-0_BIB4 Bleicher (10.1016/S0040-4039(00)01675-0_BIB9) 1998; 63 10.1016/S0040-4039(00)01675-0_BIB13 10.1016/S0040-4039(00)01675-0_BIB3 10.1016/S0040-4039(00)01675-0_BIB23 10.1016/S0040-4039(00)01675-0_BIB22 10.1016/S0040-4039(00)01675-0_BIB10 10.1016/S0040-4039(00)01675-0_BIB21 10.1016/S0040-4039(00)01675-0_BIB8 Aceto (10.1016/S0040-4039(00)01675-0_BIB6) 1979; 22 10.1016/S0040-4039(00)01675-0_BIB5 Nybäck (10.1016/S0040-4039(00)01675-0_BIB7) 1994; 115 Roush (10.1016/S0040-4039(00)01675-0_BIB11) 1985; 107 Racherla (10.1016/S0040-4039(00)01675-0_BIB14) 1992; 57 |
| References_xml | – volume: 57 start-page: 6614 year: 1992 end-page: 6617 ident: BIB14 publication-title: J. Org. Chem. contributor: fullname: Brown – volume: 78 start-page: 23 year: 2000 end-page: 26 ident: BIB2 publication-title: Chem. Eng. News contributor: fullname: Brennan – volume: 115 start-page: 31 year: 1994 end-page: 36 ident: BIB7 publication-title: Psychopharmacology contributor: fullname: Erikson – volume: 22 start-page: 174 year: 1979 end-page: 177 ident: BIB6 publication-title: J. Med. Chem. contributor: fullname: Vincek – volume: 107 start-page: 8186 year: 1985 end-page: 8190 ident: BIB11 publication-title: J. Am. Chem. Soc. contributor: fullname: Hoong – volume: 54 start-page: 10317 year: 1998 end-page: 10328 ident: BIB12 publication-title: Tetrahedron contributor: fullname: Knochel – volume: 63 start-page: 31 year: 1998 end-page: 37 ident: BIB9 publication-title: J. Org. Chem. contributor: fullname: McDonald – volume: 34 start-page: 563 year: 1995 end-page: 579 ident: BIB1 publication-title: Neuropharmacology contributor: fullname: Changeux – volume: 58 start-page: 5886 year: 1993 end-page: 5888 ident: BIB20 publication-title: J. Org. Chem. contributor: fullname: Grabowski – start-page: 1749 year: 1999 ident: WOS:000084037100011 article-title: Synthesis of macrocyclic inclusion complexes using olefin metathesis publication-title: SYNLETT contributor: fullname: Ng, PL – volume: 116 start-page: 8952 year: 1994 ident: WOS:A1994PK97900012 article-title: CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES WITH A CHIRAL TITANOCENE CATALYST - SCOPE AND LIMITATIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: WILLOUGHBY, CA – volume: 11 start-page: 316 year: 1999 ident: WOS:000079845000009 article-title: A novel enantioselective synthesis of (S)-(-)- and (R)-(+)-nornicotine via alkylation of a chiral 2-hydroxy-3-pinanone ketimine template publication-title: CHIRALITY contributor: fullname: Swango, JH – volume: 54 start-page: 10317 year: 1998 ident: WOS:000075312400008 article-title: New strategy for the preparation of nitrogen- and phosphorus-containing chiral polyfunctional secondary alcohols publication-title: TETRAHEDRON contributor: fullname: Lutz, C – volume: 10 start-page: 573 year: 1999 ident: WOS:000079213400019 article-title: Synthesis of chiral 2-(2 '-pyrrolidinyl)pyridines from (S)- and (R)-proline: potential ligands of the neuronal nicotinic acetylcholine receptors publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Che, DQ – start-page: 605 year: 1992 ident: WOS:A1992JD39400001 article-title: PRACTICAL AND USEFUL METHODS FOR THE ENANTIOSELECTIVE REDUCTION OF UNSYMMETRICAL KETONES publication-title: SYNTHESIS-STUTTGART contributor: fullname: SINGH, VK – volume: 53 start-page: 12405 year: 1997 ident: WOS:A1997XV79400007 article-title: Synthesis of Ro 25-8210 via an enantioselective oxazaborolidine-catalyzed reduction publication-title: TETRAHEDRON contributor: fullname: Hull, KG – volume: 51 start-page: 432 year: 1986 ident: WOS:A1986A261000003 article-title: CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: JADHAV, PK – volume: 64 start-page: 5299 year: 1999 ident: WOS:000081474300045 article-title: A novel method for the racemization of 5-bromonicotine publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Bleicher, LS – volume: 78 start-page: 23 year: 2000 ident: WOS:000086124600038 article-title: The good side of nicotine publication-title: CHEMICAL & ENGINEERING NEWS contributor: fullname: Brennan, MB – volume: 40 start-page: 7847 year: 1999 ident: WOS:000083043400033 article-title: A novel reductive aminocyclization for the syntheses of chiral pyrrolidines: stereoselective syntheses of (S)-nornicotine and 2-(2 '-pyrrolidyl)-pyridines publication-title: TETRAHEDRON LETTERS contributor: fullname: Loh, TP – start-page: 41 year: 1999 ident: WOS:000165482600010.30 publication-title: SYNLETT contributor: fullname: UCHI J – volume: 107 start-page: 8186 year: 1985 ident: WOS:A1985AXB4600062 article-title: DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDEHYDE ADDITION-REACTIONS OF 2-ALLYL-1,3,2-DIOXABOROLANE-4,5-DICARBOXYLIC ESTERS, A USEFUL CLASS OF TARTRATE ESTER MODIFIED ALLYLBORONATES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: ROUSH, WR – volume: 57 start-page: 6614 year: 1992 ident: WOS:A1992JZ57900045 article-title: CHIRAL SYNTHESIS VIA ORGANOBORANES .36. EXCEPTIONALLY ENANTIOSELECTIVE ALLYLBORATIONS OF REPRESENTATIVE HETEROCYCLIC ALDEHYDES AT -100-DEGREES-C UNDER SALT-FREE CONDITIONS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: RACHERLA, US – volume: 1 start-page: 615 year: 1999 ident: WOS:000083701900021 article-title: Asymmetric synthesis of the balanol heterocycle via a palladium-mediated epimerization and olefin metathesis publication-title: ORGANIC LETTERS contributor: fullname: Cook, GR – volume: 37 start-page: 4091 year: 1996 ident: WOS:A1996UP92300002 article-title: Constrained amino acids, an approach to the synthesis of 3-substituted prolines publication-title: TETRAHEDRON LETTERS contributor: fullname: Waid, PP – volume: 40 start-page: 4169 year: 1997 ident: WOS:000071343300001 article-title: Neuronal nicotinic acetylcholine receptors as targets for drug discovery publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Holladay, MW – volume: 567 start-page: 31 year: 1998 ident: WOS:000075989300007 article-title: Hydroboration-azide alkylation as efficient tandem reactions for the synthesis of chiral non racemic substituted pyrrolidines publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: Salmon, A – volume: 47 start-page: 1069 year: 1982 ident: WOS:A1982NF10900034 article-title: SYNTHESIS OF OPTICALLY-ACTIVE NICOTINOIDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CHAVDARIAN, CG – volume: 41 start-page: 759 year: 2000 ident: WOS:000165482600010.24 publication-title: TETRAHEDRON LETT contributor: fullname: SANKAR TK – volume: 22 start-page: 174 year: 1979 ident: WOS:A1979GF57700009 article-title: OPTICALLY PURE (+)-NICOTINE FROM (+/-)-NICOTINE AND BIOLOGICAL COMPARISONS WITH (-)-NICOTINE publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: ACETO, MD – volume: 58 start-page: 5886 year: 1993 ident: WOS:A1993MD98500008 article-title: DIRECT CONVERSION OF ACTIVATED ALCOHOLS TO AZIDES USING DIPHENYL PHOSPHORAZIDATE - A PRACTICAL ALTERNATIVE TO MITSUNOBU CONDITIONS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: THOMPSON, AS – volume: 292 start-page: 461 year: 2000 ident: WOS:000084929700001 article-title: Neuronal nicotinic acetylcholine receptors as novel drug targets publication-title: JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS contributor: fullname: Lloyd, GK – volume: 61 start-page: 356 year: 1996 ident: WOS:A1996TQ14600054 article-title: An efficient synthesis of the cholinergic channel activator ABT-418 publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Wittenberger, SJ – volume: 115 start-page: 31 year: 1994 ident: WOS:A1994NR46400005 article-title: PET STUDIES OF THE UPTAKE OF (S)-[C-11]NICOTINE AND (R)-[C-11]NICOTINE IN THE HUMAN BRAIN - DIFFICULTIES IN VISUALIZING SPECIFIC RECEPTOR-BINDING IN-VIVO publication-title: PSYCHOPHARMACOLOGY contributor: fullname: NYBACK, H – volume: 65 start-page: 1738 year: 2000 ident: WOS:000086020300018 article-title: Formal total synthesis of (-)-balanol: Concise approach to the hexahydroazepine segment based on RCM publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Furstner, A – start-page: 413 year: 1997 ident: WOS:A1997WY96100005 article-title: A practical procedure for the synthesis of alkyl azides at ambient temperature in dimethyl sulfoxide in high purity and yield publication-title: SYNTHESIS-STUTTGART contributor: fullname: Alvarez, SG – volume: 63 start-page: 1109 year: 1998 ident: WOS:000072215400034 article-title: A practical and efficient synthesis of the selective neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate (SIB-1508Y) publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Bleicher, LS – volume: 34 start-page: 563 year: 1995 ident: WOS:A1995RK06800001 article-title: NEURONAL NICOTINIC RECEPTORS - MOLECULAR-ORGANIZATION AND REGULATIONS publication-title: NEUROPHARMACOLOGY contributor: fullname: GALZI, JL – volume: 132 start-page: 1003 year: 1995 ident: WOS:A1995TH54900001 article-title: USEFUL SYNTHETIC TRANSFORMATIONS VIA ORGANOBORANES .1. AMINATION REACTIONS publication-title: BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE contributor: fullname: CARBONI, B – volume: 14 start-page: S695 year: 1997 ident: BCI:BCI199800105956 article-title: A novel enantioselective synthesis of (R)-(+) and (S)-(-)-nornicotine via alkylation of a chiral pinanone ketimine template publication-title: Pharmaceutical Research (New York) contributor: fullname: Swango, J. – start-page: 1907 year: 1999 ident: WOS:000084823800013 article-title: Asymmetric aminohydroxylation of heteroaromatic acrylates publication-title: SYNLETT contributor: fullname: Raatz, D – volume: 65 start-page: 861 year: 2000 ident: WOS:000085335200031 article-title: Enantiospecific synthesis of annulated nicotine analogues from D- and L-glutamic acid. Pyridotropanes publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Turner, SC – volume: 22 start-page: 174 year: 1979 ident: 10.1016/S0040-4039(00)01675-0_BIB6 publication-title: J. Med. Chem. doi: 10.1021/jm00188a009 contributor: fullname: Aceto – volume: 115 start-page: 31 year: 1994 ident: 10.1016/S0040-4039(00)01675-0_BIB7 publication-title: Psychopharmacology doi: 10.1007/BF02244748 contributor: fullname: Nybäck – volume: 107 start-page: 8186 year: 1985 ident: 10.1016/S0040-4039(00)01675-0_BIB11 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00312a062 contributor: fullname: Roush – volume: 54 start-page: 10317 year: 1998 ident: 10.1016/S0040-4039(00)01675-0_BIB12 publication-title: Tetrahedron doi: 10.1016/S0040-4020(98)00487-6 contributor: fullname: Lutz – ident: 10.1016/S0040-4039(00)01675-0_BIB19 – ident: 10.1016/S0040-4039(00)01675-0_BIB4 doi: 10.1021/jo9509723 – ident: 10.1016/S0040-4039(00)01675-0_BIB21 – ident: 10.1016/S0040-4039(00)01675-0_BIB22 – ident: 10.1016/S0040-4039(00)01675-0_BIB15 – ident: 10.1016/S0040-4039(00)01675-0_BIB8 doi: 10.1016/S0040-4039(99)01606-8 – ident: 10.1016/S0040-4039(00)01675-0_BIB3 – volume: 57 start-page: 6614 year: 1992 ident: 10.1016/S0040-4039(00)01675-0_BIB14 publication-title: J. Org. Chem. doi: 10.1021/jo00050a045 contributor: fullname: Racherla – ident: 10.1016/S0040-4039(00)01675-0_BIB16 doi: 10.1016/S0040-4020(97)00802-8 – volume: 34 start-page: 563 year: 1995 ident: 10.1016/S0040-4039(00)01675-0_BIB1 publication-title: Neuropharmacology doi: 10.1016/0028-3908(95)00034-4 contributor: fullname: Galzi – ident: 10.1016/S0040-4039(00)01675-0_BIB5 doi: 10.1021/jo991609p – ident: 10.1016/S0040-4039(00)01675-0_BIB10 – ident: 10.1016/S0040-4039(00)01675-0_BIB17 doi: 10.1055/s-1992-26174 – ident: 10.1016/S0040-4039(00)01675-0_BIB18 doi: 10.1055/s-1997-1206 – volume: 58 start-page: 5886 year: 1993 ident: 10.1016/S0040-4039(00)01675-0_BIB20 publication-title: J. Org. Chem. doi: 10.1021/jo00074a008 contributor: fullname: Thompson – ident: 10.1016/S0040-4039(00)01675-0_BIB13 doi: 10.1021/jo00354a003 – volume: 78 start-page: 23 year: 2000 ident: 10.1016/S0040-4039(00)01675-0_BIB2 publication-title: Chem. Eng. News doi: 10.1021/cen-v078n013.p023 contributor: fullname: Brennan – ident: 10.1016/S0040-4039(00)01675-0_BIB23 – volume: 63 start-page: 31 year: 1998 ident: 10.1016/S0040-4039(00)01675-0_BIB9 publication-title: J. Org. Chem. contributor: fullname: Bleicher |
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| Snippet | A short and efficient synthesis of unnatural (
R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an... A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an... |
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| SubjectTerms | alkaloids allylation asymmetric synthesis azides boron and compounds Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | A short and efficient synthesis of unnatural ( R)-nicotine |
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