Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone.

被引:13
作者
Charette, AB
Juteau, H
机构
关键词
D O I
10.1016/S0040-4020(97)01014-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.
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页码:16277 / 16286
页数:10
相关论文
共 19 条
[1]   IMPROVED PROCEDURE FOR THE SYNTHESIS OF ENANTIOMERICALLY ENRICHED CYCLOPROPYLMETHANOL DERIVATIVES [J].
CHARETTE, AB ;
PRESCOTT, S ;
BROCHU, C .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :1081-1083
[2]   DESIGN OF AMPHOTERIC BIFUNCTIONAL LIGANDS - APPLICATION TO THE ENANTIOSELECTIVE SIMMONS-SMITH CYCLOPROPANATION OF ALLYLIC ALCOHOLS [J].
CHARETTE, AB ;
JUTEAU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2651-2652
[3]  
CHARETTE AB, 1995, SYNLETT, P1197
[4]  
CHARETTE AB, IN PRESS TETRAHEDRON
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]  
FRANEKEL G, 1979, J ORG CHEM, V44, P2522
[7]   TOTAL SYNTHESIS OF (+)-BICYCLOHUMULENONE [J].
FUKUYAMA, Y ;
HIRONO, M ;
KODAMA, M .
CHEMISTRY LETTERS, 1992, (01) :167-170
[8]  
GAULT Y, 1965, B SOC CHIM FR, P742
[9]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[10]   PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].
GRIFFITH, WP ;
LEY, SV ;
WHITCOMBE, GP ;
WHITE, AD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627