Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins

被引：47

作者：

Hodgson, DM

Bailey, JM

Villalonga-Barber, C

Drew, MGB

Harrison, T

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

[2] Univ Reading, Dept Chem, Reading RG6 2AD, Berks, England

[3] Merck Sharp & Dohme Res Labs, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 20期

关键词：

D O I：

10.1039/b004870o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of diazodiketoester 8 with glyoxylates in the presence of catalytic rhodium(II) acetate generates 6,8-dioxabicyclo[3.2.1]octanes 9 and 11 in good yield. Elaboration of 9 provides a suitable alcohol 25 for acid-catalysed rearrangement to give the 2,8-dioxabicyclo[3.2.1]octane skeleton 26 of the zaragozic acids-squalestatins. More substituted diazodiketoesters 36 and 40 also undergo highly regio- and diastereoselective cycloaddition with glyoxylates to give the cycloadducts 41, 43 and 44.

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页码：3432 / 3443

页数：12

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