A SHORT-STEP SYNTHESIS OF 14,15-DINOREUDESMANOLIDES USING INTRAMOLECULAR CYCLIZATION OF AN ALLYLSILANE

被引:28
作者
KURODA, C
SHIMIZU, S
SATOH, JY
机构
[1] Department of Chemistry, St. Paul's (Rikkyo) University, Toshima-ku
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 03期
关键词
D O I
10.1039/p19900000519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
14,15-Dinoreudesman-12,6-olides, α-methylene-γ-lactones fused to a trans-decalin ring with all three possible stereochemistries, were synthesized from a simple dialdehyde monoacetal via intramolecular cyclization of ethyl 5-(2-formylcyclohexyl)-2-(trimethylsilylmethyl)pent-2-enoate. The stereoselectivity of the cyclization reaction is described.
引用
收藏
页码:519 / 524
页数:6
相关论文
共 31 条
[1]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .10. IMPROVED SYNTHESES OF (+)-TUBERIFERIN AND THE RELATED ALPHA-METHYLENE GAMMA-LACTONES AND THEIR BIOLOGICAL-ACTIVITIES [J].
ANDO, M ;
WADA, T ;
KUSAKA, H ;
TAKASE, K ;
HIRATA, N ;
YANAGI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4792-4796
[2]  
BOTTEGHI C, 1985, SYNTHESIS-STUTTGART, P592
[3]  
Cassady J. M., 1980, ANTICANCER AGENTS BA, P201
[4]  
CHAN TH, 1979, SYNTHESIS-STUTTGART, P761
[5]  
COREY EJ, 1978, TETRAHEDRON LETT, P2461
[6]  
COREY EJ, 1979, TETRAHEDRON LETT, P399
[7]  
CURPHEY TJ, 1975, J ORG CHEM, V40, P607, DOI 10.1021/jo00893a014
[8]   SYNTHESIS OF E-VINYL AND Z-VINYL ETHERS BY THE HORNER-WITTIG REACTION [J].
EARNSHAW, C ;
WALLIS, CJ ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3099-3106
[9]  
Fischer N. H., 1979, Progress in the chemistry of organic natural products. Volume 38., P47
[10]   SYNTHESIS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
GAMMILL, RB ;
WILSON, CA ;
BRYSON, TA .
SYNTHETIC COMMUNICATIONS, 1975, 5 (04) :245-268