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

被引：34

作者：

YAMAGUCHI, M

PARK, HJ

HIRAMA, M

TORISU, K

NAKAMURA, S

MINAMI, T

NISHIHARA, H

HIRAOKA, T

机构：

[1] KYUSHU INST TECHNOL, DEPT APPL CHEM, KITAKYUSHU 804, JAPAN

[2] KEIO UNIV, FAC SCI & TECHNOL, DEPT CHEM, YOKOHAMA, KANAGAWA 223, JAPAN

[3] SANKYO CO LTD, MED CHEM RES LABS, TOKYO 140, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 06期

关键词：

D O I：

10.1246/bcsj.67.1717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Selective monodesilylation of 1,8-bis(t-butyldiphenylsilyl)-1,3,5,7-octatetrayne and 1,6-bis(t-butyldiphenyl-silyl)-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.

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页码：1717 / 1725

页数：9

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