An approach to the synthesis of CP-263,114: complementary routes to the bicyclic ring system via two kinds of fragmentation reaction

被引：38

作者：

Yoshimitsu, T ^{[1
]}

Yanagiya, M ^{[1
]}

Nagaoka, H ^{[1
]}

机构：

[1] Meiji Pharmaceut Univ, Tokyo 2048588, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 28期

关键词：

bicyclic aliphatic compounds; fragmentation reactions; olefination; photochemistry;

D O I：

10.1016/S0040-4039(99)00941-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two complementary methods for the construction of the ring system of CP-263,114 (1), one relying on the Grob fragmentation reaction and the other on a sequential photolytic alkoxy radical fragmentation-reduction, are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：5215 / 5218

页数：4

相关论文

共 33 条

[1] FRAGMENTATION OF ALKOXY RADICALS - SYNTHESIS OF MACROLACTONES BY SEQUENTIAL RING EXPANSION REACTIONS [J].

ARENCIBIA, T ;

SALAZAR, JA ;

SUAREZ, E .

TETRAHEDRON LETTERS, 1994, 35 (40) :7463-7466

[2]

Armstrong A, 1998, SYNLETT, P552

[3] An approach to the synthesis of CP-263,114: A remarkably facile silyloxy-cope rearrangement [J].

Bio, MM ;

Leighton, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :890-891

[4] Stereospecific synthesis of the CP-263,114 core structure [J].

Chen, C ;

Layton, ME ;

Shair, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10784-10785

[5] INTRAMOLECULAR HYDROGEN ABSTRACTION - IODOSOBENZENE DIACETATE, AN EFFICIENT AND CONVENIENT REAGENT FOR ALKOXY RADICAL GENERATION [J].

CONCEPCION, JI ;

FRANCISCO, CG ;

HERNANDEZ, R ;

SALAZAR, JA ;

SUAREZ, E .

TETRAHEDRON LETTERS, 1984, 25 (18) :1953-1956

[6]

Dabrah TT, 1997, J ANTIBIOT, V50, P1

[7] CP-225,917 and CP-263,114: Novel ras farnesylation inhibitors from an unidentified fungus .2. Structure elucidation [J].

Dabrah, TT ;

Kaneko, T ;

Massefski, W ;

Whipple, EB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1594-1598

[8] Type II intramolecular annulations between vinylcarbenoids and furans [J].

Davies, HML ;

Calvo, R ;

Ahmed, G .

TETRAHEDRON LETTERS, 1997, 38 (10) :1737-1740

[9] HETEROLYTIC FRAGMENTATION . A CLASS OF ORGANIC REACTIONS [J].

GROB, CA ;

SCHIESS, PW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) :1-&

[10] SYNTHESIS WITH HYPOCHLOROUS ACID FUNCTIONALIZATION OF AN ISOPROPENYL GROUP - SYNTHESES OF (+)-BILOBANONE AND THE JUVABIONES [J].

HEGDE, SG ;

WOLINSKY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3148-3150

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