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.

引用

页码：1717 / 1725

页数：9

共 33 条

[21] STRUCTURES OF THE POLYMERS OBTAINED BY THE SOLID-STATE POLYMERIZATION OF DIYNE, TRIYNE, AND TETRAYNE WITH LONG-ALKYL SUBSTITUENTS
OKADA, S
HAYAMIZU, K
MATSUDA, H
MASAKI, A
NAKANISHI, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (03) : 857 - 863
[22] INTRODUCTION AND EXTENSION OF ETHYNYL GROUP USING 1,1-DICHLORO-2,2-DIFLUOROETHYLENE - CONVENIENT ROUTE TO LITHIUM ACETYLIDES AND DERIVED ACETYLENIC-COMPOUNDS
OKUHARA, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09) : 1487 - 1494
[23] SCH 31828, A NOVEL ANTIBIOTIC FROM A MICROBISPORA SP - TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES
PATEL, M
CONOVER, M
HORAN, A
LOEBENBERG, D
MARQUEZ, J
MIERZWA, R
PUAR, MS
YARBOROUGH, R
WAITZ, JA
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (06) : 794 - 797
[24] SOLUTION-SPRAY FLASH VACUUM PYROLYSIS - A NEW METHOD FOR THE SYNTHESIS OF LINEAR POLIYNES WITH ODD NUMBERS OF CC BONDS FROM SUBSTITUTED 3,4-DIALKYNYL-3-CYCLOBUTENE-1,2-DIONES
RUBIN, Y
LIN, SS
KNOBLER, CB
ANTHONY, J
BOLDI, AM
DIEDERICH, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) : 6943 - 6949
[25] PHOTOCYCLOADDITION REACTION OF SOME CONJUGATED HEXATRIYNES WITH 2,3-DIMETHYL-2-BUTENE
SHIM, SC
LEE, TS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) : 2410 - 2413
[26] VAPOR-DEPOSITION POLYMERIZATION OF BUTADIYNE
SNOW, AW
[J]. NATURE, 1981, 292 (5818) : 40 - 41
[27] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES
SONOGASHIRA, K
TOHDA, Y
HAGIHARA, N
[J]. TETRAHEDRON LETTERS, 1975, (50) : 4467 - 4470
[28] STUDIES ON DNA-CLEAVING AGENTS - SYNTHESIS OF A FUNCTIONAL DYNEMICIN ANALOG
WENDER, PA
ZERCHER, CK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) : 2311 - 2313
[29] WOLLENBERG RH, 1978, TETRAHEDRON LETT, P717
[30] EV-22, A NOVEL ANTIFUNGAL TRIACETYLENIC DIOXOLONE
WRIGHT, JJ
PUAR, MS
PRAMANIK, B
FISHMAN, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (06) : 413 - 414

← 1 2 3 4 →