A short synthesis of the bicyclic core of the zaragozic acids
β 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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π 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.
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.
## Abstract The pseudo __C__~2~βsymmetrical diketone **22** was efficiently constructed from furanβ3,4βdimethanol (**7**) using a twoβdirectional route featuring a double asymmetric dihydroxylation. Acidic hydrolysis of the cyclopentylidene acetals of **22** triggered a selective cyclization of the