Studies on the Total Synthesis of Lactonamycin: Synthesis of the Fused Pentacyclic B-F Ring Unit

被引：9

作者：

Jacques, Sylvain A. ^{[1
]}

Michaelis, Simon ^{[1
]}

Gebhardt, Bjoern ^{[1
]}

Blum, Andreas ^{[1
]}

Lebrasseur, Nathalie ^{[1
]}

Larrosa, Igor ^{[1
]}

White, Andrew J. P. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

Natural products; Total synthesis; Cross-coupling; Fused-ring systems; Oxidation; SYSTEM; MODEL; DIHYDROXYLATION; CONSTRUCTION; STRATEGY; ROUTE; MILD;

D O I：

10.1002/ejoc.201101317

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes an approach towards the total synthesis of lactonamycin with the elaboration of a key pentacyclic unit. Key steps include the synthesis of benzyl bromide 8 in eight steps and 23% overall yield starting from 4-methoxyphenol; a high-yielding Suzuki coupling between boronic ester 9 and benzyl bromide 8; and a Lewis acid mediated, intramolecular Friedel-Crafts acylation to obtain the fused BCDEF ring core.

引用

页码：107 / 113

页数：7

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