Total Synthesis of (−)-Bauhinin
The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (−)‐bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig‐Hor...
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| Published in | Helvetica chimica acta Vol. 84; no. 4; pp. 890 - 897 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Basel
Verlag Helvetica Chimica Acta
18.04.2001
Wiley |
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| Abstract | The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (−)‐bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig‐Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra‐O‐isobutyryl‐D‐glucosyl bromide 9 as the reagent in the Koenigs‐Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (−)‐bauhinin (1). |
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| AbstractList | The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (−)‐bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig‐Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra‐O‐isobutyryl‐D‐glucosyl bromide 9 as the reagent in the Koenigs‐Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (−)‐bauhinin (1). The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (-)-bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig-Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra-O-isobutyryl-D-glucosyl bromide 9 as the reagent in the Koenigs-Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (-)-bauhinin (1). |
| Author | Josien-Lefebvre, Delphine Drian, Claude Le Desmares, Guillaume |
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| References | Jotterand, N (WOS:000077257600026) 1998 NAKANISHI, T (WOS:A1994PV06700007) 1994; 42 LEDRIAN, C (WOS:A1990CM54400017) 1990; 73 PERRIN DD (WOS:000168618400014.26) 1988 MARCH J (WOS:000168618400014.23) 1992 WALDECK, DH (WOS:A1991FL73100008) 1991; 91 TAKAHASHI, K (WOS:A1978FG79100007) 1978; 26 JEGANATHAN, S (WOS:A1990CY56300019) 1990; 31 DEGUCHTENEERE, E (WOS:A1992KA25800010) 1992; 48 Forster, A (WOS:000079213400018) 1999; 10 PLOUVIER, V (WOS:A1978EZ52100040) 1978; 17 ARJONA, O (WOS:A1995RM29900046) 1995; 60 ARJONA, O (WOS:A1995QJ05200041) 1995; 36 VOGEL, P (WOS:A1990DN41300001) 1990 DWUMABADU, D (WOS:A1976DE68500001) 1976; 39 LEDRIAN, C (WOS:A1987K761500005) 1987; 70 Van Den Berg, Albert J. J. (BCI:BCI199598505443) 1995; 40 Cossy, J (WOS:A1996TM68800021) 1996; 52 DEYRUP, JA (WOS:A1972N939800048) 1972; 37 BLACK, KA (WOS:A1984TK76500028) 1984; 67 ABBOTT, TP (WOS:A1991GC08700024) 1991; 39 Forster, A (WOS:000073490400036) 1998; 39 VICIRA E (WOS:000168618400014.35) 1983; 66 ANCEREWICZ J (WOS:000168618400014.2) 1995 NAHRSTEDT, A (WOS:A1990EG19900050) 1990; 29 UEDA, K (WOS:A1983PX83000045) 1983 SOSA, A (WOS:A1977DF76600018) 1977; 16 CHEN, CC (WOS:A1985AYW5600008) 1985; 48 TURRO NJ (WOS:000168618400014.32) 1978 CHIDA, N (WOS:A1992HT70600010) 1992 WU, J (WOS:A1979HV07300011) 1979; 42 Renaut, P (WOS:000077049500011) 1998; 81 WARM, A (WOS:A1986F587600055) 1986; 51 ELLIGER, CA (WOS:A1974U143900026) 1974; 39 REYMOND, JL (WOS:A1990EH30700012) 1990; 1 LEDRIAN, C (WOS:A1989T816200018) 1989; 72 Desmares, G (WOS:000168618400013) 2001; 84 Forster, A (WOS:000075838100029) 1998; 39 Cossy, J (WOS:A1995TN50900007) 1995; 60 |
| References_xml | – volume: 39 start-page: 7097 year: 1998 ident: WOS:000075838100029 article-title: Synthesis of (+/-)-nephromopsinic acid publication-title: TETRAHEDRON LETTERS contributor: fullname: Forster, A – volume: 60 start-page: 4932 year: 1995 ident: WOS:A1995RM29900046 article-title: EVIDENCE FOR STEREOELECTRONIC CONTROL IN THE OSO4 BIS-HYDROXYLATION OF TRANS-CYCLOHEX-2-ENE-1,4-DIOLS - SYNTHESIS OF DIFFERENTIALLY PROTECTED MYOINOSITOL DERIVATIVES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ARJONA, O – volume: 67 start-page: 1612 year: 1984 ident: WOS:A1984TK76500028 article-title: OPTICAL RESOLUTION OF 7-OXABICYCLO[2.2.1]HEPT-2-ENE DERIVATIVES - DIASTEREOSELECTIVITY IN THE FORMATION OF CYANOHYDRINE-BRUCINE COMPLEXES publication-title: HELVETICA CHIMICA ACTA contributor: fullname: BLACK, KA – volume: 37 start-page: 3561 year: 1972 ident: WOS:A1972N939800048 article-title: ALKENE ISOMERIZATION - IMPROVED ONE-STEP SYNTHESIS OF TRANS CYCLOOCTENE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: DEYRUP, JA – volume: 39 start-page: 2930 year: 1974 ident: WOS:A1974U143900026 article-title: STRUCTURE AND STEREOCHEMISTRY OF SIMMONDSIN publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: ELLIGER, CA – volume: 16 start-page: 707 year: 1977 ident: WOS:A1977DF76600018 article-title: STRUCTURE OF A CYANOGLUCOSIDE OF LITHOSPERMUM-PURPUREO-CAERULEUM publication-title: PHYTOCHEMISTRY contributor: fullname: SOSA, A – start-page: 149 year: 1983 ident: WOS:A1983PX83000045 article-title: STRUCTURE OF A NEW CYANOGLUCOSIDE FROM ILEX-WARBURGII LOESN publication-title: CHEMISTRY LETTERS contributor: fullname: UEDA, K – volume: 73 start-page: 161 year: 1990 ident: WOS:A1990CM54400017 article-title: ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .11. TOTAL SYNTHESES OF (-)-CONDURITOL-B ((-)-1L-CYCLOHEX-5-ENE-1,3/2,4-TETROL) AND OF (+)-CONDURITOL-F ((+)-1D-CYCLOHEX-5-ENE-1,2,4/3-TETROL) - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF (+)-LEUCANTHEMITOL publication-title: HELVETICA CHIMICA ACTA contributor: fullname: LEDRIAN, C – volume: 48 start-page: 933 year: 1985 ident: WOS:A1985AYW5600008 article-title: BAUHININ, A NEW NITRILE GLUCOSIDE FROM BAUHINIA-CHAMPIONII publication-title: JOURNAL OF NATURAL PRODUCTS contributor: fullname: CHEN, CC – volume: 81 start-page: 2043 year: 1998 ident: WOS:000077049500011 article-title: 5a-carba-beta-D-, 5a-carba-beta-L- and 5-thio-beta-L-xylopyranosides as new orally active venous antithrombotic agents publication-title: HELVETICA CHIMICA ACTA contributor: fullname: Renaut, P – volume: 84 start-page: 880 year: 2001 ident: WOS:000168618400013 article-title: Selective formation of beta-D-glucosides of hindered alcohols publication-title: HELVETICA CHIMICA ACTA contributor: fullname: Desmares, G – volume: 39 start-page: 385 year: 1976 ident: WOS:A1976DE68500001 article-title: CONSTITUENTS OF WEST-AFRICAN MEDICINAL-PLANTS .16. GRIFFONIN AND GRIFFONILIDE, NOVEL CONSTITUENTS OF GRIFFONIA-SIMPLICIFOLIA publication-title: LLOYDIA-THE JOURNAL OF NATURAL PRODUCTS contributor: fullname: DWUMABADU, D – start-page: 245 year: 1992 ident: WOS:000168618400014.23 publication-title: ADV ORG CHEM contributor: fullname: MARCH J – volume: 91 start-page: 415 year: 1991 ident: WOS:A1991FL73100008 article-title: PHOTOISOMERIZATION DYNAMICS OF STILBENES publication-title: CHEMICAL REVIEWS contributor: fullname: WALDECK, DH – volume: 60 start-page: 8351 year: 1995 ident: WOS:A1995TN50900007 article-title: Reductive oxa ring opening of 7-oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-alpha-galactosides of carbapentopyranoses publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Cossy, J – volume: 39 start-page: 3485 year: 1998 ident: WOS:000073490400036 article-title: Preparation of an advanced intermediate for the synthesis of epi-thromboxanes publication-title: TETRAHEDRON LETTERS contributor: fullname: Forster, A – volume: 29 start-page: 3934 year: 1990 ident: WOS:A1990EG19900050 article-title: STRUCTURAL REVISION OF A PUTATIVE CYANOGENIC GLUCOSIDE FROM ILEX-AQUIFOLIUM publication-title: PHYTOCHEMISTRY contributor: fullname: NAHRSTEDT, A – volume: 70 start-page: 1703 year: 1987 ident: WOS:A1987K761500005 article-title: ACID-CATALYZED REARRANGEMENTS OF 5,6-EXO-EPOXY-7-OXABICYCLO(2.2.1)HEPT-2-YL DERIVATIVES - MIGRATORY APTITUDES OF ACYL VS ALKYL-GROUPS IN WAGNER-MEERWEIN TRANSPOSITIONS publication-title: HELVETICA CHIMICA ACTA contributor: fullname: LEDRIAN, C – volume: 48 start-page: 10603 year: 1992 ident: WOS:A1992KA25800010 article-title: TOTAL ASYMMETRIC SYNTHESES OF D-LIVIDOSAMINE AND 2-ACETAMIDO-2,3-DIDEOXY-D-ARABINO-HEXOSE DERIVATIVES publication-title: TETRAHEDRON contributor: fullname: DEGUCHTENEERE, E – volume: 42 start-page: 2251 year: 1994 ident: WOS:A1994PV06700007 article-title: STRUCTURES OF NEW AND KNOWN CYANOGLUCOSIDES FROM A NORTH-AMERICAN PLANT, PURSHIA-TRIDENTATA DC publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: NAKANISHI, T – volume: 1 start-page: 729 year: 1990 ident: WOS:A1990EH30700012 article-title: NEW CHIRAL AUXILIARIES AND NEW OPTICALLY PURE KETENE EQUIVALENTS DERIVED FROM TARTARIC-ACIDS - IMPROVED SYNTHESIS OF (-)-7-OXABICYCLO[2.2.1]HEPT-5-EN-2-ONE publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: REYMOND, JL – start-page: 474 year: 1978 ident: WOS:000168618400014.32 publication-title: MODERN MOL PHOTOCHEM contributor: fullname: TURRO NJ – start-page: 173 year: 1990 ident: WOS:A1990DN41300001 article-title: OPTICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS NEW CHIRONS publication-title: SYNLETT contributor: fullname: VOGEL, P – year: 1988 ident: WOS:000168618400014.26 publication-title: PURIFICATION LAB CHE contributor: fullname: PERRIN DD – volume: 40 start-page: 597 year: 1995 ident: BCI:BCI199598505443 article-title: Multifidin: A cyanoglucoside in the latex of Jatropha multifida publication-title: Phytochemistry (Oxford) contributor: fullname: Van Den Berg, Albert J. J. – volume: 66 start-page: 1865 year: 1983 ident: WOS:000168618400014.35 publication-title: HELV CHIM ACTA contributor: fullname: VICIRA E – volume: 42 start-page: 500 year: 1979 ident: WOS:A1979HV07300011 article-title: LITHOSPERMOSIDE AND DASYCARPONIN, CYANOGLUCOSIDES FROM THALICTRUM publication-title: JOURNAL OF NATURAL PRODUCTS contributor: fullname: WU, J – volume: 36 start-page: 1319 year: 1995 ident: WOS:A1995QJ05200041 article-title: HIGHLY DIASTEREOSELECTIVE BIS-HYDROXYLATION OF THE AMINO-DEOXY-CONDURITOL-C RING-SYSTEM - A FORMAL SYNTHESIS OF THE AMINOCYCLITOL MOIETY OF THE ANTIBIOTIC HYGROMYCIN-A publication-title: TETRAHEDRON LETTERS contributor: fullname: ARJONA, O – start-page: 1237 year: 1998 ident: WOS:000077257600026 article-title: Stereoselective synthesis of new conduramines and aminocyclitol derivatives publication-title: SYNLETT contributor: fullname: Jotterand, N – volume: 10 start-page: 567 year: 1999 ident: WOS:000079213400018 article-title: Resolution of 7-oxabicyclo[2.2.1]hept-5-en-2-one via cyclic aminals publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Forster, A – start-page: 1131 year: 1992 ident: WOS:A1992HT70600010 article-title: SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NATURALLY-OCCURRING CYANO GLUCOSIDE SIMMONDSIN publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: CHIDA, N – volume: 17 start-page: 1010 year: 1978 ident: WOS:A1978EZ52100040 article-title: PRESENCE OF LITHOSPERMOSIDE IN CERCIS-SILIQUASTRUM publication-title: PHYTOCHEMISTRY contributor: fullname: PLOUVIER, V – volume: 26 start-page: 1677 year: 1978 ident: WOS:A1978FG79100007 article-title: STUDIES ON CONSTITUENTS OF MEDICINAL-PLANTS .20. CONSTITUENT OF VINES OF MENISPERMUM-DAURICUM DC publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: TAKAHASHI, K – volume: 52 start-page: 629 year: 1996 ident: WOS:A1996TM68800021 article-title: Synthesis of (+/-)-isoavenaciolide and of (+/-)-ethisolide from (+/-)-7-oxabicyclo[2.2.1]hept-5-en-2-one publication-title: TETRAHEDRON contributor: fullname: Cossy, J – year: 1995 ident: WOS:000168618400014.2 publication-title: THESIS U LAUSANNE contributor: fullname: ANCEREWICZ J – volume: 31 start-page: 1717 year: 1990 ident: WOS:A1990CY56300019 article-title: TOTAL SYNTHESIS OF BRANCHED-CHAIN HIGHER-CARBON SUGARS - 1ST SYNTHESIS OF CALDOSE, CALDITOL AND 4-DEOXYCALDITOL STEREOISOMERS publication-title: TETRAHEDRON LETTERS contributor: fullname: JEGANATHAN, S – volume: 72 start-page: 338 year: 1989 ident: WOS:A1989T816200018 article-title: SYNTHESIS OF (-)-CONDURITOL C (1L-CYCLOHEX-5-ENE-1,2,3/4-TETROL) publication-title: HELVETICA CHIMICA ACTA contributor: fullname: LEDRIAN, C – volume: 51 start-page: 5348 year: 1986 ident: WOS:A1986F587600055 article-title: NAKED SUGARS AS SYNTHETIC INTERMEDIATES - TOTAL SYNTHESIS OF L-DAUNOSAMINE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WARM, A – volume: 39 start-page: 1488 year: 1991 ident: WOS:A1991GC08700024 article-title: PROCESSES FOR MAKING ANIMAL FEED AND PROTEIN ISOLATES FROM JOJOBA MEAL publication-title: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY contributor: fullname: ABBOTT, TP |
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| Snippet | The total synthesis of the naturally occurring cyanoglucoside (−)‐bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps... The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Total Synthesis of (−)-Bauhinin |
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