Synthesis and Reactions of Monosilylated 1,3,5-Hexatriyne and 1,3,5,7-Octatetrayne. Total Synthesis of Caryoynencins

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 ace...

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Published inBulletin of the Chemical Society of Japan Vol. 67; no. 6; pp. 1717 - 1725
Main Authors Yamaguchi, Masahiko, Park, Hyeon-Joo, Hirama, Masahiro, Torisu, Kazuhiko, Nakamura, Shigeo, Minami, Toru, Nishihara, Hiroshi, Hiraoka, Tetsuo
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.06.1994
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DIACETYLENES
L-660,631
SOLID-STATE POLYMERIZATION
POLYYNES
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Summary: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 10−4 S cm−1 when doped with SO3.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.67.1717