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

[11] ROLES OF CHROMOPHORE AND APOPROTEIN IN NEOCARZINOSTATIN ACTION
KAPPEN, LS
NAPIER, MA
GOLDBERG, IH
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (04): : 1970 - 1974
[12] ISOLATION OF A NON-PROTEIN COMPONENT AND A PROTEIN-COMPONENT FROM NEOCARZINOSTATIN (NCS) AND THEIR BIOLOGICAL-ACTIVITIES
KOIDE, Y
ISHII, F
HASUDA, K
KOYAMA, Y
EDO, K
KATAMINE, S
KITAME, F
ISHIDA, N
[J]. JOURNAL OF ANTIBIOTICS, 1980, 33 (03) : 342 - 346
[13] SYNTHESIS OF THE NEOCARZINOSTATIN CHROMOPHORE-A CORE DIYNENE STRUCTURE USING AN ETA-2-HEXACARBONYLDICOBALT MEDIATED ALDOL REACTION
MAGNUS, P
PITTERNA, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) : 541 - 543
[14] SYNTHESIS OF THE 4,5-EPOXYBICYCLO[7.3.0]DODECADIYNE NEOCARZINOSTATIN CORE STRUCTURE - SURPRISING COMPATIBILITY OF THE 4,5-EPOXIDE WITH A ETA-2-HEXACARBONYLDICOBALT MEDIATED ALDOL REACTION
MAGNUS, P
DAVIES, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) : 1522 - 1524
[15] PROPOSED STRUCTURE OF THE NEOCARZINOSTATIN CHROMOPHORE-METHYL THIOGLYCOLATE ADDUCT - A MECHANISM FOR THE NUCLEOPHILIC ACTIVATION OF NEOCARZINOSTATIN
MYERS, AG
[J]. TETRAHEDRON LETTERS, 1987, 28 (39) : 4493 - 4496
[16] A REACTION CASCADE LEADING TO 1,6-DIDEHYDRO[10]ANNULENE -] 1,5-DEHYDRONAPHTHALENE CYCLIZATION INITIATED BY THIOL ADDITION
MYERS, AG
DRAGOVICH, PS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7021 - 7022
[17] STEREOCHEMICAL ASSIGNMENT OF NEOCARZINOSTATIN CHROMOPHORE - STRUCTURES OF NEOCARZINOSTATIN CHROMOPHORE METHYL THIOGLYCOLATE ADDUCTS
MYERS, AG
PROTEAU, PJ
HANDEL, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) : 7212 - 7214
[18] ENANTIOSELECTIVE SYNTHESIS OF THE EPOXY DIYNE CORE OF NEOCARZINOSTATIN CHROMOPHORE
MYERS, AG
HARRINGTON, PM
KUO, EY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 694 - 695
[19] SYNTHETIC STUDIES ON THE COMPOUNDS RELATED TO NEOCARZINOSTATIN CHROMOPHORE .2. SYNTHESIS OF THE OPEN-CHAIN (E)-DIENEDIYNE AND (Z)-DIENEDIYNE SYSTEMS AND ITS APPLICATION TO THE SYNTHESIS OF A STRAIN-RELEASED CYCLIC ANALOG
NAKATANI, K
ARAI, K
YAMADA, K
TERASHIMA, S
[J]. TETRAHEDRON, 1992, 48 (15) : 3045 - 3060
[20] SYNTHESIS AND CYTOTOXICITY OF THE ACYCLIC (E)-DIENEDIYNE AND (Z)-DIENEDIYNE SYSTEMS RELATED TO NEOCARZINOSTATINE CHROMOPHORE
NAKATANI, K
ARAI, K
HIRAYAMA, N
MATSUDA, F
TERASHIMA, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (16) : 2323 - 2326

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