Synthesis of (-)-erythrodiene via intramolecular Pd-catalyzed Zn-ene reaction

被引:18
作者
Oppolzer, W [1 ]
Flachsmann, F [1 ]
机构
[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
关键词
spiro compounds; ene reactions; transmetalation; diastereoselection;
D O I
10.1016/S0040-4039(98)00991-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly diastereoselective synthesis of (-)-Erythrodiene was achieved via an intramolecular Pd-catalyzed Znene reaction as the key step. It was found that Pd(OAc)(2)/Bu3P was a superior catalyst for this reaction to Pd(PPh3)(4). (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5019 / 5022
页数:4
相关论文
共 16 条
[1]   A STEREOSELECTIVE TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-ERYTHRODIENE [J].
HUANG, H ;
FORSYTH, CJ .
TETRAHEDRON LETTERS, 1993, 34 (49) :7889-7890
[2]   ANTI SELECTIVE SPIROCARBOMERCURATION - SYNTHESIS AND STEREOCHEMISTRY OF THE SPIROBICYCLIC SESQUITERPENES SPIROJATAMOL AND ERYTHRODIENE [J].
HUANG, H ;
FORSYTH, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2773-2779
[3]   PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].
KNOCHEL, P ;
SINGER, RD .
CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188
[4]   HIGHLY-ACTIVE PD(0) CATALYST FROM PD(OAC)2-BU3P COMBINATION IN UNTAPPED 1/1 RATIO - PREPARATION, REACTIVITY, AND P-31-NMR [J].
MANDAI, T ;
MATSUMOTO, T ;
TSUJI, J ;
SAITO, S .
TETRAHEDRON LETTERS, 1993, 34 (15) :2513-2516
[5]   Palladium-catalysed intramolecular cyclisations of olefinic propargylic carbonates and application to the diastereoselective synthesis of enantiomerically pure (-)-alpha-thujone [J].
Oppolzer, W ;
Pimm, A ;
Stammen, B ;
Hume, WE .
HELVETICA CHIMICA ACTA, 1997, 80 (03) :623-639
[6]   INTRAMOLECULAR, STOICHIOMETRIC (LI, MG, ZN) AND CATALYTIC (NI, PD, PT) METALLO-ENE REACTIONS IN ORGANIC-SYNTHESIS [J].
OPPOLZER, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (01) :38-52
[7]   New ethylzinc reagents with remarkable properties in palladium-catalyzed zinc-ene reactions [J].
Oppolzer, W ;
Schroder, F ;
Kahl, S .
HELVETICA CHIMICA ACTA, 1997, 80 (07) :2047-2057
[8]  
OPPOLZER W, 1994, TETRAHEDRON LETT, V35, P7939, DOI 10.1016/S0040-4039(00)78390-0
[9]  
Oppolzer W., 1991, COMPREHENSIVE ORGANI, V5, P29
[10]  
Oppolzer W., 1994, ORGANOMETALLIC REAGE, P161