Synthesis and reactions of monosilylated 1,3,5-hexatriyne and 1,3,5,7-octatrayne. Total synthesis and caryoynencins

M. Yamaguchi, H. J. Park, M. Hirama, K. Torisu, S. Nakamura, T. Minami, H. Nishihara, T. Hiraoka

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31 Citations (Scopus)

Abstract

Selective monodesilylation of 1,8-bis(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1,6-bis(t-butyldiphenylsilyl)-1,3,5-hexatriyne with lithiated phenylacetylene gave unstable 1-(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1-(t-butyldiphenylsilyl)-1,3,5-hexatriyne, respectively. The terminal acetylenes on lithiation added to aldehydes and a ketone giving polyynols in high yields. The reaction was applied to the synthesis of polyyne antibiotics, caryoynencins. Polymerization of the terminal octatetrayne on an ITO-coated glass plate gave a film, which showed conductivity of 10-4S cm-1 when doped with SO3.

Original languageEnglish
Pages (from-to)1717-1725
Number of pages9
JournalBulletin of the Chemical Society of Japan
Volume67
Issue number6
DOIs
Publication statusPublished - 1994 Aug 25

ASJC Scopus subject areas

  • Chemistry(all)

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