Synthetic studies on the DEF-rings of FR182877 and hexacyclinic acid

被引：25

作者：

Clarke, PA

Grist, M

Ebden, M

Wilson, C

Blake, AJ

机构：

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

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

来源：

TETRAHEDRON | 2005年 / 61卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

transannular; lodocyclisation; natural products; medium sized rings;

D O I：

10.1016/j.tet.2004.10.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of model DEF-rings of the polyketide anti tumor natural products FR182877 and hexacyclinic acid has been achieved. The key steps in the synthesis are an intramolecular Pd(0) catalyzed allylic substitution reaction, which was used to generate a 9-membered carbocycle, and a novel transannular iodocyclization reaction which furnished the DF-rings of both natural products. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：353 / 363

页数：11

相关论文

共 40 条

[31] A practical total synthesis of plaunotol via highly Z-selective Wittig olefination of α-acetal ketones [J].

Tago, K ;

Arai, M ;

Kogen, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (13) :2073-2078

[32] INFLUENCE OF A TRANSITION-METAL ON THE REGIOCHEMISTRY OF RING CLOSURES - APPROACH TO MEDIUM-RING COMPOUNDS [J].

TROST, BM ;

VERHOEVEN, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (06) :1595-1597

[33] CYCLIZATION CATALYZED BY PALLADIUM(0) - INITIAL STUDIES AND MACROLIDE FORMATION [J].

TROST, BM ;

VERHOEVEN, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (14) :4743-4763

[34] PALLADIUM-CATALYZED 1,3-OXYGEN-TO-CARBON ALKYL SHIFTS - BASIC STUDIES [J].

TROST, BM ;

RUNGE, TA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7550-7559

[35] An enantioselective synthesis of FR182877 provides a chemical rationalization of its structure and affords multigram quantities of its direct precursor [J].

Vanderwal, CD ;

Vosburg, DA ;

Weiler, S ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5393-5407

[36] A synthesis of (+)-FR182877, featuring tandem transannular Diels-Alder reactions inspired by a postulated biogenesis [J].

Vosburg, DA ;

Vanderwal, CD ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (17) :4552-4553

[37] Chromatography with silver nitrate [J].

Williams, CM ;

Mander, LN .

TETRAHEDRON, 2001, 57 (03) :425-447

[38]

Yoshimura S, 2002, J ANTIBIOT, V55, pC1

[39] A new antimitotic substance, FR182877 - III. Structure determination [J].

Yoshimura, S ;

Sato, B ;

Kinoshita, T ;

Takase, S ;

Terano, H .

JOURNAL OF ANTIBIOTICS, 2000, 53 (06) :615-622

[40] A convergent total synthesis of hemibrevetoxin B [J].

Zakarian, A ;

Batch, A ;

Holton, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7822-7824

← 1 2 3 4 →