Total synthesis of oxacyclic macrodiolide natural products

被引：293

作者：

Kang, EJ ^{[1
]}

Lee, E ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Nat Sci, Dept Chem, Seoul 151747, South Korea

来源：

CHEMICAL REVIEWS | 2005年 / 105卷 / 12期

关键词：

D O I：

10.1021/cr040629a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A review of the total synthesis of oxacyclic macrodiolide natural products is presented. Focus is on macrodiolide; with oxolane moieties like pamamycin and amphidinolide; with oxane/oxene moieties as SCH 351448 and swinholide A; structures incorporating cyclic acetal units as cycloviracin B1 and glucolipsin A; and macrodiolide that exhibits cyclic hemiketal structural units like boromycin, tartrolon B, debromoaplysiatoxin and aplysiatoxin. Various processes for the syntheses of these products are described and these include intramolecular selenoetherification of homoallylic alcohols, epoxide formation/dimethylcuprate reaction, silverion-catalyzed cyclization of a chiral allenol, radical cyclization of alcoxyacrylates, electrophilic addition to cyclic oxocarbenium ions, esterification reactions of different monomeric hydroxy carboxylic acids, template-directed cyclodimerizaiton reaction of hydroxy carboxylic acids, and ring-closing metathesis reaction of an open diester intermediate.

引用

页码：4348 / 4378

页数：31

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