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Studies towards the synthesis of the zaragozic acids: Synthesis of the bicyclic acetal core of zaragozic acid C

✍ Scribed by Ian Paterson; Klaus Feßner; M.Raymond V. Finlay

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
258 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The bicyclic core 6 of zaragozic acid C (7) was prepared by the epoxide cyclisation reaction 21 --4 22 --~ 15. Acetal 15 was also obtained by acid-promoted rearrangement of the isomeric acetal 19.

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✍ Ian Paterson; Klaus Feßner; M.Raymond V Finlay; Mark F Jacobs 📂 Article 📅 1996 🏛 Elsevier Science 🌐 French ⚖ 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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A total synthesis of (+)-zaragozic acid C is described. Key steps are an acid-mediated acetonide deprotection-dithiane removal-ketalisation procedure, providing selectively the 2,8dioxabicyclo[3.2.1]octane core of the natural product, and the simultaneous introduction of the C3, C4 and C5 carboxylic