A NOVEL MONOCYCLIC DIENEDIYNE SYSTEM - SYNTHESIS AND MODE OF AROMATIZATION

被引：16

作者：

TOSHIMA, K

YANAGAWA, K

OHTA, K

KANO, T

NAKATA, M

机构：

[1] Department of Applied Chemistry, Keio University, Kohoku-ku, Yokohama, 223

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)76761-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The novel monocyclic dienediyne 2, which is a simplified analogue of the neocarzinostatin chromophore (1), was synthesized from D-xylitol via conversion of the keto-aldehyde 13 into the highly strained 10-membered ring compound 14 by a simple intramolecular aldol condensation as the key step. The mode of cycloaromatization of 2 by a thiol addition, reminiscent of the chemistry of 1, was also demonstrated.

引用

页码：1573 / 1576

页数：4

共 35 条

[31] CYCLOAROMATIZATION AND DNA CLEAVAGE OF NOVEL ENYNE-ALLENE SYSTEMS
TOSHIMA, K
OHTA, K
OHTSUKA, A
MATSUMURA, S
NAKATA, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) : 1406 - 1407
[32] A NEW ROUTE TO 10-MEMBERED RING ANALOGS OF NEOCARZINOSTATIN CHROMOPHORE
WEHLAGE, T
KREBS, A
LINK, T
[J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6625 - 6628
[33] GENERAL METHODOLOGY FOR THE SYNTHESIS OF NEOCARZINOSTATIN CHROMOPHORE ANALOGS - INTRAMOLECULAR CHROMIUM-MEDIATED CLOSURES FOR STRAINED-RING SYNTHESIS
WENDER, PA
MCKINNEY, JA
MUKAI, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) : 5369 - 5370
[34] STUDIES ON DNA-ACTIVE AGENTS - THE SYNTHESIS OF THE PARENT CARBOCYCLIC SUBUNIT OF NEOCARZINOSTATIN CHROMOPHORE-A
WENDER, PA
HARMATA, M
JEFFREY, D
MUKAI, C
SUFFERT, J
[J]. TETRAHEDRON LETTERS, 1988, 29 (08) : 909 - 912
[35] STUDIES ON DNA CLEAVING AGENTS - SYNTHESIS AND CHEMICALLY-INDUCED CYCLOAROMATIZATION OF A MONOCYCLIC NEOCARZINOSTATIN CHROMOPHORE ANALOG
WENDER, PA
TEBBE, MJ
[J]. TETRAHEDRON LETTERS, 1991, 32 (37) : 4863 - 4866

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