SYNTHESIS AND REACTIONS OF MONOSILYLATED 1,3,5-HEXATRIYNE AND 1,3,5,7-OCTATETRAYNE - TOTAL SYNTHESIS OF CARYOYNENCINS

Authors
YAMAGUCHI M PARK HJ HIRAMA M TORISU K NAKAMURA S MINAMI T NISHIHARA H HIRAOKA T
Citation
M. Yamaguchi et al., SYNTHESIS AND REACTIONS OF MONOSILYLATED 1,3,5-HEXATRIYNE AND 1,3,5,7-OCTATETRAYNE - TOTAL SYNTHESIS OF CARYOYNENCINS, Bulletin of the Chemical Society of Japan, 67(6), 1994, pp. 1717-1725
Citations number
33
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
67
Issue
6
Year of publication
1994
Pages
1717 - 1725
Database
ISI
SICI code
0009-2673(1994)67:6<1717:SAROM1>2.0.ZU;2-O
Abstract
Selective monodesilylation of 1,8-bis(t-butyldiphenylsilyl)-1,3,5,7-oc tatetrayne and 1,6-bis(t-butyldiphenyl-silyl)-1,3,5-hexatriyne with li thiated phenylacetylene gave unstable 1-(t-butyldiphenylsilyl)-1,3,5,7 -octatetrayne and 1-(t-butyldiphenylsilyl)-1,3,5-hexatriyne, respectiv ely. The terminal acetylenes on lithiation added to aldehydes and a ke tone 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.