AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF THE MACRODIOLIDE (-)-(RRR)-COLLETALLOL

被引：23

作者：

DOMMERHOLT, FJ ^{[1
]}

THIJS, L ^{[1
]}

ZWANENBURG, B ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,TOERNOOIVELD,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 11期

关键词：

D O I：

10.1016/0040-4039(91)80367-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (-)-colletallol, a naturally occurring macrodiolide, has been completed in 26 steps. An essential step in the sequence is the photo-induced rearrangement of an alpha,beta-epoxy diazomethyl ketone to produce a 4-hydroxy-2-alkenoate.

引用

页码：1495 / 1498

页数：4

共 7 条

[1] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[2] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[3] FUNGAL PRODUCTS .5. ABSOLUTE STEREOCHEMISTRY OF COLLETODIOL AND STRUCTURES OF RELATED METABOLITES OF COLLETOTRICHUM-CAPSICI [J].

MACMILLAN, J ;

SIMPSON, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (14) :1487-1493

[4]

NICOLAOU KC, 1977, TETRAHEDRON, V33, P3041

[5]

SCHNURRENBERGER P, 1987, LIEBIGS ANN CHEM, P733

[6] A GENERAL STEREOSPECIFIC SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS [J].

THIJS, L ;

DOMMERHOLT, FJ ;

LEEMHUIS, FMC ;

ZWANENBURG, B .

TETRAHEDRON LETTERS, 1990, 31 (45) :6589-6592

[7] SYNTHESES OF (+/-)-PYRENOPHORIN AND (+/-)-COLLETALLOL [J].

WAKAMATSU, T ;

YAMADA, S ;

OZAKI, Y ;

BAN, Y .

TETRAHEDRON LETTERS, 1985, 26 (16) :1989-1992

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