TOTAL SYNTHESIS OF (+/-)-EPICUBENOL

被引:5
作者
CANE, DE
TANDON, M
机构
[1] Department of Chemistry, Brown University, Providence, RI 02912, Box H
关键词
D O I
10.1016/S0040-4039(00)73497-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The sesquiterpenoid microbial metabolite (+/-)-epicubenol (1) has been synthesized in 8 steps from a readily available diene aldehyde (7) using an intramolecular Diels-Alder reaction.
引用
收藏
页码:5351 / 5354
页数:4
相关论文
共 13 条
[1]   EPICUBENOL SYNTHASE AND THE ENZYMATIC CYCLIZATION OF FARNESYL DIPHOSPHATE [J].
CANE, DE ;
TANDON, M ;
PRABHAKARAN, PC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8103-8106
[2]   SELECTIVE REDUCTION OF MONOSUBSTITUTED AND DISUBSTITUTED OLEFINS BY SODIUM-BOROHYDRIDE AND COBALT(II) [J].
CHUNG, SK .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (06) :1014-1016
[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]   TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN [J].
EVANS, DA ;
KALDOR, SW ;
JONES, TK ;
CLARDY, J ;
STOUT, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7001-7031
[5]   SESQUITERPENOIDS FROM ACTINOMYCETES - CADIN-4-ENE-1-OL [J].
GERBER, NN .
PHYTOCHEMISTRY, 1971, 10 (01) :185-&
[6]   WITTIG REACTION USING METHYLSULFINYL CARBANION-DIMETHYL SULFOXIDE [J].
GREENWALD, R ;
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (04) :1128-&
[7]   SYNTHETIC METHODS .8. HYDROXYLATION OF CARBONYL-COMPOUNDS VIA SILYL ENOL ETHERS [J].
HASSNER, A ;
REUSS, RH ;
PINNICK, HW .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23) :3427-3429
[8]   STEREOCHEMICAL CONTROL OF ANGULAR METHYLATION OF FUSED RING KETONES [J].
JOHNSON, WS ;
SAUSEN, GN ;
HINDERSI.RR ;
PAPPO, R ;
ALLEN, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (11) :2181-+
[9]  
OHTA Y, 1967, TETRAHEDRON LETT, P2073
[10]   REDUCTION OF CARBONYL-COMPOUNDS VIA HYDROSILYLATION .4. HIGHLY REGIOSELECTIVE REDUCTIONS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
OJIMA, I ;
KOGURE, T .
ORGANOMETALLICS, 1982, 1 (10) :1390-1399