Desulfurization of sultones with simultaneous methylenation

被引:17
作者
Metz, P
Seng, D
Plietker, B
机构
[1] Organisch-Chemisches Institut, Universität Münster, D-48149 Münster
关键词
D O I
10.1016/0040-4039(96)00728-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Desulfurization of the delta-sultones 2 with simultaneous formation of an exocyclic defin is achieved by alkylation of 2 with (iodomethyl)trimethylsilane and subsequent treatment of the resultant products 7 with tetra-n-butylammonium fluoride. Application of this two-step procedure to sultone 8 leads to 1,3-diene 10, an intermediate for the synthesis of the highly oxygenated 1,10-seco-eudesmanolides eriolanin and eriolangin. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:3841 / 3844
页数:4
相关论文
共 22 条
[1]   IMPROVED PALLADIUM-CATALYZED 1,4-HALOACYLOXYLATION AND 1,4-DIACYLOXYLATION OF CYCLIC CONJUGATED DIENES [J].
BACKVALL, JE ;
GRANBERG, KL ;
HOPKINS, RB .
ACTA CHEMICA SCANDINAVICA, 1990, 44 (05) :492-499
[2]  
BACKVALL JE, 1984, J ORG CHEM, V49, P4619
[3]  
Buglass A.J., 1991, CHEM SULPHONIC ACIDS, P789
[4]  
DELIMA C, 1992, SYNLETT, P133
[5]   CARBONIUM-ION REARRANGEMENTS CONTROLLED BY THE PRESENCE OF A SILYL GROUP [J].
FLEMING, I ;
PATEL, SK ;
URCH, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :115-124
[6]   SESQUITERPENE LACTONES - TOTAL SYNTHESIS OF (+/-)-ERIOLANIN AND (+/-)-ERIOLANGIN [J].
GRIECO, PA ;
OGURI, T ;
GILMAN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5886-5891
[7]   ONE-POT, ONE-CARBON AND MULTICARBON HOMOLOGATION OF ALKYL-HALIDES - REACTION OF GRIGNARD-REAGENTS WITH CHLOROIODOMETHANE [J].
HAHN, RC ;
TOMPKINS, J .
TETRAHEDRON LETTERS, 1990, 31 (07) :937-940
[8]   TERMINAL OLEFINS FROM THE FLUORIDE-INDUCED ELIMINATION OF BETA-SILYLSULFONES [J].
KOCIENSKI, PJ .
TETRAHEDRON LETTERS, 1979, (28) :2649-2650
[9]   ERIOLANGIN AND ERIOLANIN, NOVEL ANTILEUKEMIC SECO-EUDESMANOLIDES FROM ERIOPHYLLUM-LANATUM [J].
KUPCHAN, SM ;
BAXTER, RL ;
CHIANG, CK ;
GILMORE, CJ ;
BRYAN, RF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (21) :842-843
[10]  
METZ P, 1994, ANGEW CHEM INT EDIT, V33, P2195, DOI 10.1002/anie.199421951