Total synthesis of macrosphelide A by way of palladium-catalyzed carbonylative esterification

被引：33

作者：

Kusaka, S ^{[1
]}

Dohi, S ^{[1
]}

Doi, T ^{[1
]}

Takahashi, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 49期

关键词：

macrolactone; palladium catalyst; carbonylation; natural product synthesis;

D O I：

10.1016/j.tetlet.2003.09.186

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We achieved the total synthesis of macrosphelide A. as part of a combinatorial library of its analogues. The key intermediate. the seco-acid derivative, was prepared from the corresponding vinyl iodide using sequential carbonylative esterification. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8857 / 8859

页数：3

共 37 条

[1] Total synthesis of (+)-macrosphelides A, C, E, F, and G based on enzymatic function [J].

Akita, H ;

Nakamura, H ;

Ono, M .

CHIRALITY, 2003, 15 (04) :352-359

[2] PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].

BODEN, EP ;

KECK, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395

[3] TOTAL SYNTHESIS OF OCTALACTIN-A AND OCTALACTIN-B [J].

BUSZEK, KR ;

SATO, N ;

JEONG, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5511-5512

[4]

COREY EJ, 1976, TETRAHEDRON LETT, P3405

[5] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].

COREY, EJ ;

NICOLAOU, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616

[6] The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride.: The merged stereochemical impact of α- and β-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles [J].

Evans, DA ;

Allison, BD ;

Yang, MG ;

Masse, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10840-10852

[7] Chelation-controlled stannylacetylene additions to β-alkoxy aldehydes promoted by alkylaluminum halide Lewis acids [J].

Evans, DA ;

Halstead, DP ;

Allison, BD .

TETRAHEDRON LETTERS, 1999, 40 (24) :4461-4462

[8] Chelate-controlled carbonyl addition reactions. The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride [J].

Evans, DA ;

Allison, BD ;

Yang, MG .

TETRAHEDRON LETTERS, 1999, 40 (24) :4457-4460

[9] Macrosphelide B suppressed metastasis through inhibition of adhesion of sLex/E-selectin molecules [J].

Fukami, A ;

Iijima, K ;

Hayashi, M ;

Komiyama, K ;

Omura, S .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2002, 291 (04) :1065-1070

[10] New members of the macrosphelides from Microsphaeropsis sp FO-5050IV [J].

Fukami, A ;

Taniguchi, Y ;

Nakamura, T ;

Rho, MC ;

Kawaguchi, K ;

Hayashi, M ;

Komiyama, K ;

Omura, S .

JOURNAL OF ANTIBIOTICS, 1999, 52 (05) :501-504

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