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A short synthesis of the bicyclic core of the zaragozic acids

✍ Scribed by Pierre Fraisse; Issam Hanna; Jean-Yves Lallemand


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
228 KB
Volume
39
Category
Article
ISSN
0040-4039

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Studies towards the synthesis of the zar
✍ Ian Paterson; Klaus Feßner; M.Raymond V Finlay; Mark F Jacobs πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 French βš– 253 KB

Model studies towards the bicyclic acetal core 1 of the zaragozic acids, based on the epoxide cyclisation reaction 4 ---) 3, are described. Epoxide 14 provides the desired bicyclic acetal skeleton 16, while epoxide 27 leads through 28 to an isomeric acetal 30.

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## Abstract The pseudo __C__~2~‐symmetrical diketone **22** was efficiently constructed from furan‐3,4‐dimethanol (**7**) using a two‐directional route featuring a double asymmetric dihydroxylation. Acidic hydrolysis of the cyclopentylidene acetals of **22** triggered a selective cyclization of the