An iodocyclisation/elimination approach to a DEF-ring core of FR182877

被引：21

作者：

Clarke, PA

Grist, M

Ebden, M

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] AstraZeneca Charnwood, Med Chem, Loughborough LE11 5RH, Leics, England

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2003.11.105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transannular iodocyclisation reaction has directly furnished the DEF-ring system of the natural product FR182877. However, higher yields of the DEF-ring system are obtained via transannular iodocyclisation followed by elimination of acetic acid. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：927 / 929

页数：3

相关论文

共 15 条

[1] A one-step synthesis of tetrahydropyranopyranones from carbonyl compounds [J].

Armstrong, A ;

Goldberg, FW ;

Sandham, DA .

TETRAHEDRON LETTERS, 2001, 42 (27) :4585-4587

[2] Synthesis of a model DEF-ring core of hexacyclinic acid [J].

Clarke, PA ;

Grist, M ;

Ebden, M ;

Wilson, C .

CHEMICAL COMMUNICATIONS, 2003, (13) :1560-1561

[3] On the Diels-Alder reactions and the Lewis acid induced rearrangements of 6-fumaryl 1,3,8-nonatrienes [J].

Clarke, PA ;

Davie, RL ;

Peace, S .

TETRAHEDRON LETTERS, 2002, 43 (15) :2753-2756

[4]

Evans DA, 2002, ANGEW CHEM INT EDIT, V41, P1787, DOI 10.1002/1521-3773(20020517)41:10<1787::AID-ANIE1787>3.0.CO

[5]

2-V

[6] Enantioselective total synthesis of (-)-xialenon A [J].

Hodgson, DM ;

Galano, JM ;

Christlieb, M .

CHEMICAL COMMUNICATIONS, 2002, (20) :2436-2437

[7]

Höfs R, 2000, ANGEW CHEM INT EDIT, V39, P3258, DOI 10.1002/1521-3773(20000915)39:18<3258::AID-ANIE3258>3.0.CO

[8]

2-Q

[9]

Sato B, 2000, J ANTIBIOT, V53, P123, DOI 10.7164/antibiotics.53.204

[10] Synthetic studies on FR182877: an asymmetric synthesis of the AB ring moiety of FR182877 via a diastereoselective intramolecular Diels-Alder reaction [J].

Suzuki, T ;

Nakada, M .

TETRAHEDRON LETTERS, 2002, 43 (18) :3263-3267