BRONSTED ACID-CATALYZED ELECTROPHILIC SUBSTITUTION OF INDOLE BY ALLYLIC ALCOHOLS IN LITHIUM PERCHLORATE DIETHYL-ETHER - APPLICATION TO THE TOTAL SYNTHESIS OF YUEHCHUKENE

被引:41
作者
HENRY, KJ [1 ]
GRIECO, PA [1 ]
机构
[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
关键词
D O I
10.1039/c39930000510
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel carbon-carbon bond-forming reaction between indole and beta,beta-disubstituted allylic alcohols in lithium perchlorate-diethyl ether containing a catalytic amount of a Bronsted acid is described; the reaction has been applied to a total synthesis of yuehchukene.
引用
收藏
页码:510 / 512
页数:3
相关论文
共 12 条
[1]   SYNTHESIS OF YUEHCHUKENE AND SOME ANALOGS - A GENERAL-APPROACH [J].
BERGMAN, J ;
VENEMALM, L .
TETRAHEDRON, 1992, 48 (04) :759-768
[2]   TOTAL SYNTHESIS OF YUEHCHUKENE [J].
BERGMAN, J ;
VENEMALM, L .
TETRAHEDRON LETTERS, 1988, 29 (24) :2993-2994
[3]   BIOMIMETIC SYNTHESIS OF YEUHCHUKENE [J].
CHENG, KF ;
KONG, YC ;
CHAN, TY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (02) :48-49
[4]   DIRECT SUBSTITUTION OF SECONDARY ALLYLIC ALCOHOLS WITH O-SILYLATED KETENE ACETALS IN 3.0 M LITHIUM PERCHLORATE-DIETHYL ETHER - AN ALTERNATIVE TO THE [1,3] SIGMATROPIC REARRANGEMENT OF ALLYL VINYL ETHERS [J].
GRIECO, PA ;
COLLINS, JL ;
HENRY, KJ .
TETRAHEDRON LETTERS, 1992, 33 (33) :4735-4738
[5]   YUEHCHUKENE - A NOVEL INDOLE ALKALOID WITH ANTI-IMPLANTATION ACTIVITY [J].
KONG, YC ;
CHENG, KF ;
CAMBIE, RC ;
WATERMAN, PG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (02) :47-48
[6]   A VERSATILE SYNTHETIC ROUTE TO THE ANTI-IMPLANTATION AGENT, YUEHCHUKENE, AND ITS ANALOGS [J].
KUTNEY, JP ;
LOPEZ, FJ ;
HUANG, SP ;
KUROBE, H ;
FLOGAUS, R ;
PIOTROWSKA, K ;
RETTIG, SJ .
CANADIAN JOURNAL OF CHEMISTRY, 1991, 69 (06) :949-971
[7]  
KUTNEY JP, 1989, HETEROCYCLES, V28, P565
[8]   NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - CONJUGATE ADDITIONS WITHOUT THE ENONE [J].
MAGNUS, P ;
LACOUR, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (10) :3993-3994
[9]   EFFICIENT METHODS FOR OXIDATION OF ALCOHOLS [J].
NARASAKA, K ;
MORIKAWA, A ;
SAIGO, K ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) :2773-2776
[10]   LITHIUM PERCHLORATE-ASSISTED SUBSTITUTION-REACTIONS OF ALLYLIC ACETATES AND ALLYLIC ALCOHOLS [J].
PEARSON, WH ;
SCHKERYANTZ, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :2986-2987