A triple umpolung sequence for the preparation of highly substituted indanes.

被引:7
作者
Harrowven, DC [1 ]
Browne, R [1 ]
机构
[1] UNIV NOTTINGHAM,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1016/0040-4020(96)00907-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The paper describes a new method for the diastereoselective construction of highly substituted indanes. The key step involves a triple umpolung sequence in which a 2-lithio-2-vinyl-1,3-dithiane is first united with an aryl halide to form a ketenedithioacetal. Transmetallation of the aryl halide with an alkyllithium reagent then generates an alkyl halide and a 2-indanyl-2-lithio-1,3-dithiane. Finally, these combine to complete the sequence. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:14951 / 14960
页数:10
相关论文
共 32 条
[31]   MODEL STUDIES FOR ANTHRACYCLINONE SYNTHESIS - CHEMISTRY OF 1-LITHIO-3,3,6,6-TETRAMETHOXYCYCLOHEXA-1,4-DIENE, AN UMPOLUNG FOR QUINONE [J].
SWENTON, JS ;
JACKSON, DK ;
MANNING, MJ ;
RAYNOLDS, PW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (19) :6182-6188
[32]   CONJUGATE ADDITION OF DITHIANYLIDENE ANIONS TO ALPHA,BETA-UNSATURATED KETONES - AN APPLICATION TO THE TOTAL SYNTHESIS OF (+/-)-AROMATIN AND (+/-)-CONFERTIN [J].
ZIEGLER, FE ;
FANG, JM ;
TAM, CC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7174-7181