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

DM Hodgson, JM Bailey, C Villalonga-Barber…

Index: Hodgson, David M.; Bailey, James M.; Villalonga-Barber, Carolina; Drew, Michael G. B.; Harrison, Timothy Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 20 p. 3432 - 3443

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Citation Number: 43

Abstract

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 ...