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A Simple Synthesis of a Model of the Tetracyclic Bisketal Lactone Mainframe of Saudin

✍ Scribed by Guillermo R. Labadie; Liliana E. Luna; Raquel M. Cravero; Manuel González-Sierra

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
101 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

The partial structure 2 of the bisketal-type, tetracyclic saudin (1), an important natural product, was de novo synthesized. A key step was the Jones oxidation of the epoxide 3, which gave rise to epoxide-ring opening, followed by acetal hydrolysis, alcohol oxidation, and, finally, intramolecular acetal formation. The resulting key intermediate was finally oxidized to the target lactone 2.

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