Issue 20, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

David M. Hodgson,†*ab   James M. Bailey,ab   Carolina Villalonga-Barber,a   Michael G. B. Drewb  and  Timothy Harrisonc  

* Corresponding authors

a Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, UK

b Department of Chemistry, University of Reading, Whiteknights, Reading, UK

c Merck Sharp & Dohme Research Laboratories, Neuroscience Research Centre, Terlings Park, Harlow, Essex, UK

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 cycloaddition with glyoxylates to give the cycloadducts 41, 43 and 44.

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DOI
https://doi.org/10.1039/B004870O
Article type
Paper
Submitted
19 Jun 2000
Accepted
16 Aug 2000
First published
03 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3432-3443

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

D. M. Hodgson, J. M. Bailey, C. Villalonga-Barber, M. G. B. Drew and T. Harrison, J. Chem. Soc., Perkin Trans. 1, 2000, 3432 DOI: 10.1039/B004870O

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