A HIGHLY STEREOSELECTIVE SYNTHESIS OF THE VERSATILE CHIRAL SYNTHONS POSSESSING 2 STEREOGENIC CENTERS, THE FORMAL TOTAL SYNTHESES OF (-)-OUDEMANSIN-A, (-)-OUDEMANSIN-B, AND (-)-OUDEMANSIN-X

被引：16

作者：

AKITA, H

CHEN, CY

NAGUMO, S

机构：

[1] School of Pharmaceutical Science, Toho University, Funabashi, Chiba, 274, 2-2-1, Miyama

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 07期

关键词：

D O I：

10.1016/0957-4166(94)80158-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A highly stereoselective synthesis of the versatile chiral synthons possessing two stereogenic centers, (2R,3R)-8 and (2S,3S)-8 was achieved and the application of (2R,3R)-8 into the formal total syntheses of (-)-oudemansins A(2), B(3), and X(4) were described

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页码：1207 / 1210

页数：4

相关论文

共 10 条

[1] TOTAL SYNTHESIS OF (-)-OUDEMANSIN-X BASED ON ENZYMATIC RESOLUTION USING IMMOBILIZED LIPASE [J].

AKITA, H ;

UMEZAWA, I ;

NOZAWA, M ;

NAGUMO, S .

TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :757-760

[2] DETERMINATION OF ABSOLUTE STRUCTURE OF (-)-OUDEMANSIN-B [J].

AKITA, H ;

MATSUKURA, H ;

OISHI, T .

TETRAHEDRON LETTERS, 1986, 27 (44) :5397-5400

[3] THE ABSOLUTE-CONFIGURATION OF OUDEMANSIN TOTAL SYNTHESIS OF (-)-OUDEMANSIN [J].

AKITA, H ;

KOSHIJI, H ;

FURUICHI, A ;

HORIKOSHI, K ;

OISHI, T .

TETRAHEDRON LETTERS, 1983, 24 (19) :2009-2010

[4]

AKITA H, 1983, CHEM PHARM BULL, V31, P4384

[5] ANTIBIOTICS FROM BASIDIOMYCETES .9. OUDEMANSIN, AN ANTIFUNGAL ANTIBIOTIC FROM OUDEMANSIELLA-MUCIDA (SCHRADER EX FR) HOEHNEL (AGARICALES) [J].

ANKE, T ;

HECHT, HJ ;

SCHRAMM, G ;

STEGLICH, W .

JOURNAL OF ANTIBIOTICS, 1979, 32 (11) :1112-1117

[6] ANTIBIOTICS FROM BASIDIOMYCETES .23. OUDEMANSIN-X, A NEW ANTIFUNGAL E-BETA-METHOXYACRYLATE FROM OUDEMANSIELLA-RADICATA (RELHAN EX-FR) SING [J].

ANKE, T ;

WERLE, A ;

BROSS, M ;

STEGLICH, W .

JOURNAL OF ANTIBIOTICS, 1990, 43 (08) :1010-1011

[7] ANTIBIOTICS FROM BASIDIOMYCETES .18. STROBILURIN C AND OUDEMANSIN-B, 2 NEW ANTI-FUNGAL METABOLITES FROM XERULA SPECIES (AGARICALES) [J].

ANKE, T ;

BESL, H ;

MOCEK, U ;

STEGLICH, W .

JOURNAL OF ANTIBIOTICS, 1983, 36 (06) :661-666

[8] TOTAL SYNTHESIS OF ANTIBIOTIC (-)-OUDEMANSIN-X UTILIZING L-QUEBRACHITOL AS A CHIRAL POOL [J].

CHIDA, N ;

YAMADA, K ;

OGAWA, S .

CHEMISTRY LETTERS, 1992, (04) :687-690

[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[10] STEREOSELECTIVE REDUCTION OF BETA-KETO-ESTERS WITH ZINC BOROHYDRIDE - STEREOSELECTIVE SYNTHESIS OF ERYTHRO-3-HYDROXY-2-ALKYLPROPIONATES [J].

NAKATA, T ;

OISHI, T .

TETRAHEDRON LETTERS, 1980, 21 (17) :1641-1644