TOTAL SYNTHESIS OF THE TETRAQUINANE DITERPENOID (+-)-CRINIPELLIN-B

被引:101
作者
PIERS, E
RENAUD, J
机构
[1] Department of Chemistry, University of British Columbia, Vancouver, British Columbia, V6T 1Z1, 2036 Main Mall, University Campus
关键词
D O I
10.1021/jo00053a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Beginning with 2-methyl-2-cyclopenten-1-one (5), the total synthesis of the structurally novel tetraquinane diterpenoid (+/-)-crinipellin B (4) has been accomplished via a 22-step sequence of reactions.
引用
收藏
页码:11 / 13
页数:3
相关论文
共 20 条
[1]   ANTIBIOTICS FROM BASIDIOMYCETES .21. CRINIPELLINS, THE 1ST NATURAL-PRODUCTS WITH A TETRAQUINANE SKELETON [J].
ANKE, T ;
HEIM, J ;
KNOCH, F ;
MOCEK, U ;
STEFFAN, B ;
STEGLICH, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (08) :709-711
[2]   SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS (ACYLOINS) - DIRECT OXIDATION OF ENOLATES USING 2-SULFONYLOXAZIRIDINES [J].
DAVIS, FA ;
VISHWAKARMA, LC ;
BILLMERS, JM ;
FINN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3241-3243
[3]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[4]  
Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13
[5]   ANIONIC APPROACHES TO THE CONSTRUCTION OF CYCLOPENTANOIDS [J].
HUDLICKY, T ;
PRICE, JD .
CHEMICAL REVIEWS, 1989, 89 (07) :1467-1486
[6]   ANTIBIOTICS FROM BASIDIOMYCETES .7. CRINIPELLIN, A NEW ANTIBIOTIC FROM THE BASIDIOMYCETOUS FUNGUS CRINIPELLIS-STIPITARIA (FR) PAT [J].
KUPKA, J ;
ANKE, T ;
OBERWINKLER, F ;
SCHRAMM, G ;
STEGLICH, W .
JOURNAL OF ANTIBIOTICS, 1979, 32 (02) :130-135
[7]   A NOVEL REGIOSPECIFIC AND STEREOSPECIFIC HYDROHALOGENATION REACTION OF 2-PROPYNOIC ACID AND ITS DERIVATIVES [J].
MA, S ;
LU, XY ;
LI, ZG .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :709-713
[8]   SYNTHETIC STUDIES TOWARDS CRINIPELLINS - CONSTRUCTION OF THE FUNCTIONALIZED C-20 TETRAQUINANE CARBON FRAMEWORK THROUGH CATIONIC ENONE-OLEFIN CYCLIZATION STRATAGEM [J].
MEHTA, G ;
RAO, KS ;
REDDY, MS .
TETRAHEDRON LETTERS, 1988, 29 (39) :5025-5028
[9]   MODEL STUDIES TOWARDS CRINIPELLIN DITERPENES AND PANICULATINE-TYPE LYCOPODIUM ALKALOIDS FROM A COMMON TRIQUINANE PRECURSOR [J].
MEHTA, G ;
RAO, KS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) :1578-1580
[10]   SYNTHETIC APPROACH TO NOVEL CRINIPELLIN DITERPENES - CONSTRUCTION OF THE FUNCTIONALIZED C20-TETRAQUINANE FRAMEWORK [J].
MEHTA, G ;
RAO, KS ;
REDDY, MS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (04) :693-700