Synthesis of Macrosporin and Related 9,10-Anthraquinones by Biomimetic Polyketide Aromatization and Cyclization of 6-Benzylresorcylates

被引：16

作者：

Cordes, Jens ^{[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 | 2013年 / 2013卷 / 07期

基金：

欧洲研究理事会;

关键词：

Natural products; Quinones; Fused-ring systems; Annulation; Oxidation; METABOLIC PRODUCTS; ENDOPHYTIC FUNGUS; PORRI ELLIOTT; BIOACTIVE METABOLITES; ANTHRAQUINONES; BIOSYNTHESIS; ANGELICOIN; PIGMENTS;

D O I：

10.1002/ejoc.201201480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes the synthesis of an array of 9,10-anthraquinones 2 by initial preparation of 6-benzylresorcylates 3 from oxo-dioxinone precursors 4 and their subsequent conversion to anthrones by cyclization and oxidation. Resorcylates 3 were obtained by an improved two-step procedure from oxo ester 5 and acyl chlorides 6. These methods were applied in a seven-step synthesis of the fungal natural product macrosporin (1).

引用

页码：1318 / 1326

页数：9

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