Download PDF
Synlett 1991; 1991(9): 651-653
DOI: 10.1055/s-1991-20829
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis and Cycloaromatization of a Neocarzinostatin Chromophore Analogue Equipped with an Intramolecular Nucleophile

Masahiro Hirama* , Masahiko Tokuda, Kenshu Fujiwara
  • *Department of Chemistry, Faculty of Science, Tohoku University, Sendai 980, Japan
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A new 10 membered ring analogue of neocarzinostatin chromophore 4 [12-(2-acetylthioethyl)-7,7-dimethyl-5-oxobicyclo-[8.3.0]trideca-1(2),10(11)-diene-3,8-diyne] equipped with the acetylthioethane group undergoes intramolecular conjugate addition of the corresponding thiolate under weakly basic methanolysis conditions leading to reductive cycloaromatization to give the benz[5,6]indeno[1,2-b]thiophene ring system. The intermediacy of the phenyl radical 19 has been supported by the abstraction of carbon-bound deuterium.

      >