Diastereodivergent synthesis of the C8–C18 precursor and C1′–C11′ subunit of pamamycin 607 induced by a chiral sulfoxide group
A key step in obtaining the C8–C18 and C1′–C11′ fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center α to the tetrahydrofuran ring, was the chelation controlled E–Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far bee...
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| Published in | Tetrahedron letters Vol. 41; no. 15; pp. 2737 - 2740 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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01.04.2000
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| Abstract | A key step in obtaining the C8–C18 and C1′–C11′ fragments of pamamycin 607, which differ by the
syn- and
anti-configuration of one chiral center α to the tetrahydrofuran ring, was the chelation controlled
E–Z-isomerization of the substituted vinyl tetrahydrofuran intermediate
3a which has so far been obtained only in the more stable
E-configuration. |
|---|---|
| AbstractList | A key step in obtaining the C8–C18 and C1′–C11′ fragments of pamamycin 607, which differ by the
syn- and
anti-configuration of one chiral center α to the tetrahydrofuran ring, was the chelation controlled
E–Z-isomerization of the substituted vinyl tetrahydrofuran intermediate
3a which has so far been obtained only in the more stable
E-configuration. A key step in obtaining the C8-C18 and C1'-C11' fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center alpha to the tetrahydrofuran ring, was the chelation controlled E-Z-isomerization of the substituted vinyl tetrahydrofuran intermediate 3a which has so far been obtained only in the more stable E-configuration. (C) 2000 Elsevier Science Ltd. Air rights reserved. |
| Author | Salom-Roig, Xavier J Hanquet, Gilles Solladié, Guy |
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| CitedBy_id | crossref_primary_10_1016_j_tetlet_2004_11_135 crossref_primary_10_1002_ejoc_200700320 crossref_primary_10_1002_anie_200701749 crossref_primary_10_1039_C8CC05571H crossref_primary_10_1002_1521_3773_20020415_41_8_1392__AID_ANIE1392_3_0_CO_2_G crossref_primary_10_1039_c2ob26801a crossref_primary_10_1002_ange_200701749 crossref_primary_10_1016_S0040_4039_02_00655_X crossref_primary_10_1002_ejoc_200901513 crossref_primary_10_1021_ol902290v crossref_primary_10_1016_S0040_4039_00_01308_3 crossref_primary_10_1271_bbb_65_2630 crossref_primary_10_1002_chin_200026208 crossref_primary_10_1016_S0040_4039_01_00921_2 crossref_primary_10_1039_b509578f crossref_primary_10_1002_1099_0690_200207_2002_13_2112__AID_EJOC2112_3_0_CO_2 crossref_primary_10_1021_jo100774n crossref_primary_10_1016_j_tet_2007_08_046 crossref_primary_10_1016_S0040_4039_01_01665_3 crossref_primary_10_1016_j_tet_2006_03_093 crossref_primary_10_1016_S0040_4039_01_01044_9 crossref_primary_10_1016_j_tetlet_2008_06_059 crossref_primary_10_1016_S0957_4166_03_00125_3 |
| Cites_doi | 10.7164/antibiotics.32.673 10.1021/jo00093a022 10.1016/S0040-4020(01)80580-9 10.1002/jobm.3620320510 10.7164/antibiotics.41.1196 10.1016/0040-4039(96)00638-7 10.1016/S0040-4039(01)81074-1 10.1021/jo00075a057 10.1016/S0040-4039(99)02117-6 10.1021/jo00091a037 10.1016/0040-4039(95)00471-N 10.1016/S0006-291X(81)80102-7 10.1016/S0040-4039(00)80798-4 10.1021/ja00415a024 10.1016/0040-4039(91)80696-4 10.1002/(SICI)1099-0690(199909)1999:9<2303::AID-EJOC2303>3.0.CO;2-8 10.1021/jo00935a033 10.1021/ja00330a045 |
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| Keywords | (+)-NONACTIC ACID ANTIBIOTICS REDUCTION STREPTOMYCES-ALBONIGER SUBSTANCE |
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| References | C NMR (CDCl 339–345. (a) Bartlett, P. A.; Meadows, J. D.; Ottow, E. 79–88. 344–350. Walkup, R. D.; Kim, S. W. H NMR (200 MHz, CDCl (a) Walkup, R. D.; Park, G. C NMR (50 MHz, CDCl (a) MacCann, P. A.; Pogell, B. M. 50 MHz 7.0 Hz, 3H), 1.20 (d 2303–2307. Kondo, S.; Yasui, K.; Katayama, M.; Marumo, S.; Kondo, T.; Hattori, H. 17 a) (2 19 7550–7559. ) , - . 1.3 Hz, 3H), 1.10–1.80 (m, 7H), 1.99–2.21 (m, 1H), 2.74–2.91 (m, 1H), 3.02–3.16 (m, 1H), 3.96–4.04 (m, 1H), 4.41–4.54 (m, 1H), 7.32–7.48 (m, 6H), 7.66–7.73 (m, 4H 0.93 (t 5304–5311. (b) Solladié, G.; Domı́nguez, C. 3 6 0.6, acetone 3091–3094. 8 Solladié, G.; Salom-Roig, X. J.; Hanquet, G. : 3898–3901. 169.0, 136.0, 134.7, 134.2, 129.6, 127.6, 98.8, 79.8, 79.1, 70.7, 42.5, 39.6, 31.2, 30.6, 28.6, 27.2, 19.6, 17.7, 14.0, 11.8; (b) (2 Natsume, M.; Yasui, K.; Kondo, S.; Marumo, S. 1196–1204. (b) Walkup, R. D.; Kim, S. W. 6486–6490. (c) Mavropoulos, I.; Perlmutter, P. 200 MHz 551–554. 3433–3441. (c) Chou, W.-G.; Pogell, B. M. 7 Hz, 3H), 1.06 (s, 9H), 1.52 (s, 9H), 1.73 (t 173.9, 80.9, 80.5, 77.3, 69.0, 46.3, 41.1, 39.5, 30.9, 29.2, 28.1, 19.1, 14.4, 14.2. H NMR (CDCl Hydrogenation of the double bond resulted in an 85:15 distereomeric ratio of the expected product and a mixture ot three diastereoisomers. See (a) Krueger, S. A.; Bryson, T. 0.6 acetone 5861–5864. ] 3751–3754. (d) Bloch, R.; Girard, C.; Mandville, G. Honda, T.; Ishige, H.; Araki, J.; Akimoto, S.; Hirayama, K.; Tsubuki, M. 7 Hz 3H), 1.45 (s, 9H), 1.32–1.81 (m, 8H), 1.89–2.08 (m, 2H), 2.48–2.34 (m, 1H), 2.82 (broad s, 1H), 3.78–3.98 (m, 2H), 4.06–4.19 (m, 1H 167.1, 165.6, 136.0, 134.7, 134.5, 129.6, 127.6, 96.3, 82.5, 79.0, 71.1, 42.6, 39.6, 31.1, 29.2, 28.5, 27.2, 19.6, 17.8, 14.7, 14.2; (c) (2 3167; (b) Trost, B. M.; Runge, T. A. 0.67 (t 3665–3673. (e) Mandville, G.; Bloch, R. 0.67 CHCl 3087–3090. 0.74 (t 5505–5508 (racemic form). (b) Walkup, R. D.; Kim, S. W.; Wagy, S. D. 673–678. (b) Stengel, C.; Reinhardt, G.; Grafe, U. (a) Kondo, S.; Yasui, K.; Natsume, M.; Katayama, M.; Marumo, S. 7.0 Hz, 3H), 1.06 (s, 9H), 1.22–1.44 (m, 4H), 1.45 (s, 9H), 1.70 (s, 3H), 1.61–1.76 (m, 2H), 1.78–1.84 (m, 2H), 2.38–2.64 (m, 2H), 3.95–4.04 (m, 1H), 4.32–4.47 (m, 1H), 7.32–7.48 (m, 6H), 7.67–7.73 (m, 4H STENGEL, C (WOS:A1992KC62700007) 1992; 32 Mandville, G (WOS:A1997YG78900022) 1997; 8 Mandville, G (WOS:000084006600038) 1999; 1999 BARTLETT, PA (WOS:A1984TH18100045) 1984; 106 MCCANN, PA (WOS:A1979HD17600001) 1979; 32 Solladie, G (WOS:000084947700027) 2000; 41 SOLLADIE, G (WOS:A1994NX38400022) 1994; 59 KRUEGER SA (WOS:000086555200052.7) 1981; 103 CHOU, WG (WOS:A1981LR98700049) 1981; 100 WALKUP, RD (WOS:A1994NU18100037) 1994; 59 WALKUP, RD (WOS:A1988Q903400014) 1988; 29 WALKUP, RD (WOS:A1993MF51600057) 1993; 58 WALKUP, RD (WOS:A1995QW87000004) 1995; 36 NATSUME, M (WOS:A1991FP28300028) 1991; 32 KONDO, S (WOS:A1988Q149000005) 1988; 41 HONDA, T (WOS:A1992GX95500007) 1992; 48 KONDO, S (WOS:A1987L250100024) 1987; 28 Mavropoulos, I (WOS:A1996UN05600038) 1996; 37 cr-split#-10.1016/S0040-4039(00)00251-3_BIB8.3 cr-split#-10.1016/S0040-4039(00)00251-3_BIB9.2 cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.3 10.1016/S0040-4039(00)00251-3_BIB12 cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.4 cr-split#-10.1016/S0040-4039(00)00251-3_BIB7.1 cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.5 cr-split#-10.1016/S0040-4039(00)00251-3_BIB7.2 cr-split#-10.1016/S0040-4039(00)00251-3_BIB8.1 cr-split#-10.1016/S0040-4039(00)00251-3_BIB8.2 cr-split#-10.1016/S0040-4039(00)00251-3_BIB9.1 cr-split#-10.1016/S0040-4039(00)00251-3_BIB1.2 cr-split#-10.1016/S0040-4039(00)00251-3_BIB2.1 cr-split#-10.1016/S0040-4039(00)00251-3_BIB2.2 cr-split#-10.1016/S0040-4039(00)00251-3_BIB2.3 cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.1 10.1016/S0040-4039(00)00251-3_BIB10 cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.2 10.1016/S0040-4039(00)00251-3_BIB11 10.1016/S0040-4039(00)00251-3_BIB3 10.1016/S0040-4039(00)00251-3_BIB6 cr-split#-10.1016/S0040-4039(00)00251-3_BIB1.1 10.1016/S0040-4039(00)00251-3_BIB5 |
| References_xml | – volume: 29 start-page: 5505 year: 1988 ident: WOS:A1988Q903400014 article-title: SYNTHESIS OF THE C1'-C11' PORTION OF PAMAMYCIN-607 VIA A STEREOSELECTIVE OXYMERCURATION OF A GAMMA-SILYLOXYALLENE AND A STEREOSPECIFIC MAGNESIUM-METHANOL REDUCTION publication-title: TETRAHEDRON LETTERS contributor: fullname: WALKUP, RD – volume: 8 start-page: 3665 year: 1997 ident: WOS:A1997YG78900022 article-title: A novel and efficient stereoselective synthesis of the southern part of pamamycin-607 publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Mandville, G – volume: 32 start-page: 673 year: 1979 ident: WOS:A1979HD17600001 article-title: PAMAMYCIN - NEW ANTIBIOTIC AND STIMULATOR OF AERIAL MYCELIA FORMATION publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: MCCANN, PA – volume: 106 start-page: 5304 year: 1984 ident: WOS:A1984TH18100045 article-title: ENANTIODIVERGENT SYNTHESES OF (+)-NONACTIC AND (-)-NONACTIC ACID AND THE TOTAL SYNTHESIS OF NONACTIN publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: BARTLETT, PA – volume: 48 start-page: 79 year: 1992 ident: WOS:A1992GX95500007 article-title: A SYNTHESIS OF (+)-NONACTIC ACID BY MEANS OF THE SULFUR-YLIDE REARRANGEMENT publication-title: TETRAHEDRON contributor: fullname: HONDA, T – volume: 59 start-page: 3898 year: 1994 ident: WOS:A1994NX38400022 article-title: A SHORT ASYMMETRIC-SYNTHESIS OF (+)-NONACTIC ACID AND (-)-8-EPI-NONACTIC ACID-INDUCED BY A CHIRAL SULFOXIDE GROUP publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SOLLADIE, G – volume: 28 start-page: 5861 year: 1987 ident: WOS:A1987L250100024 article-title: STRUCTURE OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE OF STREPTOMYCES-ALBONIGER publication-title: TETRAHEDRON LETTERS contributor: fullname: KONDO, S – volume: 41 start-page: 1196 year: 1988 ident: WOS:A1988Q149000005 article-title: ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY OF PAMAMYCIN-607, AN AERIAL MYCELIUM-INDUCING SUBSTANCE FROM STREPTOMYCES-ALBONIGER publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: KONDO, S – volume: 41 start-page: 551 year: 2000 ident: WOS:000084947700027 article-title: Stereoselective synthesis towards the C8-C18 subunit of pamamycin-607 induced by a chiral sulfoxide group publication-title: TETRAHEDRON LETTERS contributor: fullname: Solladie, G – volume: 37 start-page: 3751 year: 1996 ident: WOS:A1996UN05600038 article-title: The total synthesis of pamamycin 607 .1. Synthesis of a C1'-C11' synthon publication-title: TETRAHEDRON LETTERS contributor: fullname: Mavropoulos, I – volume: 58 start-page: 6486 year: 1993 ident: WOS:A1993MF51600057 article-title: SYNTHESES OF ENANTIOMERICALLY PURE TETRAHYDROFURAN BUILDING-BLOCKS FOR NACTIN AND PAMAMYCIN ANTIBIOTICS VIA AN ENZYMATICALLY RESOLVED GAMMA-HYDROXYALLENE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WALKUP, RD – volume: 100 start-page: 344 year: 1981 ident: WOS:A1981LR98700049 article-title: PAMAMYCIN INHIBITS NUCLEOSIDE AND INORGANIC-PHOSPHATE TRANSPORT IN STAPHYLOCOCCUS-AUREUS publication-title: BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS contributor: fullname: CHOU, WG – volume: 32 start-page: 339 year: 1992 ident: WOS:A1992KC62700007 article-title: A SIMPLE SCREENING-PROCEDURE FOR MICROBIAL PHASE-TRANSFER MEDIATORS CONVEYING ANIONS publication-title: JOURNAL OF BASIC MICROBIOLOGY contributor: fullname: STENGEL, C – volume: 1999 start-page: 2303 year: 1999 ident: WOS:000084006600038 article-title: Towards the total synthesis of pamamycin-607: Preparation of the eastern part-(C-8-C-18 fragment) publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Mandville, G – volume: 103 start-page: 7550 year: 1981 ident: WOS:000086555200052.7 publication-title: J AM CHEM SOC contributor: fullname: KRUEGER SA – volume: 59 start-page: 3433 year: 1994 ident: WOS:A1994NU18100037 article-title: SYNTHESES OF THE LOWER PORTIONS OF THE PAMAMYCINS FROM GAMMA-(SILYLOXY)ALLENES USING STEREOSELECTIVE CYCLIZATION, REDUCTION, AND ALDEHYDE ADDITION METHODOLOGIES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WALKUP, RD – volume: 36 start-page: 3091 year: 1995 ident: WOS:A1995QW87000004 article-title: SYNTHESIS OF A C-1-C-14 SUBUNIT OF THE MACRODIOLIDE ANTIBIOTICS PAMAMYCIN-607 AND PAMAMYCIN-635B publication-title: TETRAHEDRON LETTERS contributor: fullname: WALKUP, RD – volume: 32 start-page: 3087 year: 1991 ident: WOS:A1991FP28300028 article-title: THE STRUCTURES OF 4 NEW PAMAMYCIN HOMOLOGS ISOLATED FROM STREPTOMYCES-ALBONIGER publication-title: TETRAHEDRON LETTERS contributor: fullname: NATSUME, M – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB1.1 doi: 10.7164/antibiotics.32.673 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB8.2 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB8.3 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB8.1 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB9.2 doi: 10.1021/jo00093a022 – ident: 10.1016/S0040-4039(00)00251-3_BIB11 doi: 10.1016/S0040-4020(01)80580-9 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.4 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB1.2 doi: 10.1002/jobm.3620320510 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB2.1 doi: 10.7164/antibiotics.41.1196 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.3 doi: 10.1016/0040-4039(96)00638-7 – ident: 10.1016/S0040-4039(00)00251-3_BIB3 doi: 10.1016/S0040-4039(01)81074-1 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.2 doi: 10.1021/jo00075a057 – ident: 10.1016/S0040-4039(00)00251-3_BIB6 doi: 10.1016/S0040-4039(99)02117-6 – ident: 10.1016/S0040-4039(00)00251-3_BIB10 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB2.2 doi: 10.1021/jo00091a037 – ident: 10.1016/S0040-4039(00)00251-3_BIB5 doi: 10.1016/0040-4039(95)00471-N – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB2.3 doi: 10.1016/S0006-291X(81)80102-7 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.1 doi: 10.1016/S0040-4039(00)80798-4 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB7.2 doi: 10.1021/ja00415a024 – ident: 10.1016/S0040-4039(00)00251-3_BIB12 doi: 10.1016/0040-4039(91)80696-4 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB4.5 doi: 10.1002/(SICI)1099-0690(199909)1999:9<2303::AID-EJOC2303>3.0.CO;2-8 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB7.1 doi: 10.1021/jo00935a033 – ident: #cr-split#-10.1016/S0040-4039(00)00251-3_BIB9.1 doi: 10.1021/ja00330a045 |
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| Snippet | A key step in obtaining the C8–C18 and C1′–C11′ fragments of pamamycin 607, which differ by the
syn- and
anti-configuration of one chiral center α to the... A key step in obtaining the C8-C18 and C1'-C11' fragments of pamamycin 607, which differ by the syn- and anti-configuration of one chiral center alpha to the... |
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| Title | Diastereodivergent synthesis of the C8–C18 precursor and C1′–C11′ subunit of pamamycin 607 induced by a chiral sulfoxide group |
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