A STEREOSELECTIVE TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-ERYTHRODIENE

被引:19
作者
HUANG, H [1 ]
FORSYTH, CJ [1 ]
机构
[1] UNIV MINNESOTA,DEPT CHEM,MINNEAPOLIS,MN 55455
关键词
D O I
10.1016/S0040-4039(00)61502-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Erythrodiene, a unique spirobicyclic sesquiterpene hydrocarbon from the Caribbean gorgonian cord Erythropodium caribaeorum, has been synthesized from 4-isopropylcyclohexanol in 8-steps and approximately 16% overall yield. The synthesis features a stereoselective intramolecular carbomercuration reaction as the key step.
引用
收藏
页码:7889 / 7890
页数:2
相关论文
共 8 条
[1]  
ALDERDICE M, 1990, ORG SYNTH, V7, P351
[2]   SESQUITERPENOIDS .64. .143. SPIROJATAMOL, A NEW SKELETAL SESQUITERPENOID OF NARDOSTACHYS-JATAMANSI ROOTS [J].
BAGCHI, A ;
OSHIMA, Y ;
HIKINO, H .
TETRAHEDRON, 1990, 46 (05) :1523-1530
[3]  
BOAVENTURA MA, 1987, B SOC CHIM FR, P1015
[4]   SIMPLE METHOD FOR FAST AND STEREOSELECTIVE SYNTHESIS OF ENOXYSILANES OF ALDEHYDES AND KETONES [J].
CAZEAU, P ;
MOULINES, F ;
LAPORTE, O ;
DUBOUDIN, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 201 (02) :C9-C13
[5]   CYCLIZATION OF ACETYLENIC CARBONYL-COMPOUNDS VIA THEIR SILYL ENOL ETHER DERIVATIVES - A NEW INTRAMOLECULAR C-VINYLATION INDUCED BY MERCURY(II) SALTS - STEREOCHEMISTRY AND FUNCTIONALIZATION OF THE INTERMEDIATE VINYLMERCURIAL [J].
DROUIN, J ;
BOAVENTURA, MA ;
CONIA, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1726-1729
[6]  
FENICAL, COMMUNICATION
[7]  
FORSYTH CJ, 1989, J AM CHEM SOC, V112, P3497
[8]   ERYTHRODIENE - A NEW SPIROBICYCLIC SESQUITERPENE OF A RARE SKELETAL CLASS FROM THE CARIBBEAN GORGONIAN CORAL ERYTHROPODIUM-CARIBAEORUM [J].
PATHIRANA, C ;
FENICAL, W ;
CORCORAN, E ;
CLARDY, J .
TETRAHEDRON LETTERS, 1993, 34 (21) :3371-3372