NEW ROUTE TO (-)-FRONTALIN AND (-)-MALYNGOLIDE VIA EPOXYKETONE REARRANGEMENT

被引：33
作者：
ASAOKA, M
HAYASHIBE, S
SONODA, S
TAKEI, H
机构：
[1] Department of Life Chemistry, Tokyo Institute of Technology, Midoriku, Yokohama
来源：
TETRAHEDRON | 1991年 / 47卷 / 34期
关键词：
(-)-FRONTALINE; (-)-MALYNGOLIDE; RING CONTRACTION; EPOXYKETONE; REARRANGEMENT;
D O I：
10.1016/S0040-4020(01)96151-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of the title compounds by utilizing BF3.Et2O catalyzed ring contraction of 2,3-epoxycyclohexanones leading to 2-alkyl-2-formylcyclopentanones is described.
引用
收藏
页码：6967 / 6974
页数：8
相关论文
共 16 条
[1]   CONSTRUCTION OF CHIRAL QUARTERNARY CARBON CENTERS USING 3-SUBSTITUTED 5-TRIMETHYLSILYL-2-CYCLOHEXENONES - SYNTHESIS OF (+)-ALPHA-CUPARENONE [J].
ASAOKA, M ;
TAKENOUCHI, K ;
TAKEI, H .
TETRAHEDRON LETTERS, 1988, 29 (03) :325-328
[2]   DIASTEREOSELECTIVE 1,4-ADDITION OF VARIOUS NUCLEOPHILES TO 5-TRIMETHYLSILYL-2-CYCLOHEXENONE - SYNTHESIS OF (+)-RAMULOSIN [J].
ASAOKA, M ;
SONODA, S ;
FUJII, N ;
TAKEI, H .
TETRAHEDRON, 1990, 46 (05) :1541-1552
[3]  
HO TL, 1988, CARBOCYCLE CONSTRUCT, P579
[4]   AN ENANTIOCONTROLLED SYNTHESIS OF (-)-MALYNGOLIDE [J].
HONDA, T ;
IMAI, M ;
KEINO, K ;
TSUBUKI, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10) :2677-2680
[5]   NEW ASPECTS OF OXYPALLADATION OF ALKENES [J].
HOSOKAWA, T ;
MURAHASHI, SI .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (02) :49-54
[6]   STEREOSELECTIVE SYNTHESIS OF MARINE ANTIBIOTIC (-)-MALYNGOLIDE AND ITS STEREOISOMERS [J].
ICHIMOTO, I ;
MACHIYA, K ;
KIRIHATA, M ;
UEDA, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (03) :657-662
[7]   ON THE STEREOCHEMISTRY OF THE BF3-CATALYZED REARRANGEMENT OF (+)-ISOPHORONE OXIDE [J].
KUNISCH, F ;
HOBERT, K ;
WELZEL, P .
TETRAHEDRON LETTERS, 1985, 26 (49) :6039-6042
[8]  
MATSUO K, 1981, CHEM PHARM BULL, V29, P3047
[9]   SYNTHESIS OF OPTICALLY-ACTIVE PHEROMONES [J].
MORI, K .
TETRAHEDRON, 1989, 45 (11) :3233-3298
[10]  
OHOTA H, 1989, TETRAHEDRON, V45, P5469
12