Studies Towards the Synthesis of the Zaragozic Acids: A Novel Epoxide Cyclization Approach to the Formation of the Bicyclic Acetal Core. -Model studies towards the synthesis of the bicyclic core of zaragozic acid are reported. The strategy is based on an epoxide cyclization reaction. Thus, treatmen
Studies towards the synthesis of the zaragozic acids: A novel epoxide cyclisation approach to the formation of the bicyclic acetal core
✍ Scribed by Ian Paterson; Klaus Feßner; M.Raymond V Finlay; Mark F Jacobs
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 253 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.
📜 SIMILAR VOLUMES
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.
Reaction of diazoketodiester 11 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate gives predominantly the 6,8-dioxabicyclo[3.2.1]octane 13. Acid-catalysed rearrangement of the corresponding alcohol 14 favours at equilibrium the 2,8-dioxabicyclo[3.2.1]octane skeleton