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Stereoselective synthesis of polyoxygenated atisane-type diterpenoids

✍ Scribed by Antonio Abad; Consuelo Agulló; Ana C Cuñat; Ismael Navarro

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
79 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new stereoselective approach to polyoxygenated atisane-type diterpenes starting from (S)-(+)-carvone is described.

The key steps involve an intramolecular Diels-Alder reaction, an unusual intramolecular diazo ketone cyclopropanation of an unsaturated ketone, and a regioselective endocyclic cleavage of a cyclopropyl carbinyl radical as key synthetic steps. The synthesis of the bioactive polyoxygenated atisanes atis-16(17)-en-3,14-dione (2) and 3R-hydroxy-atis-16(17)-en-2,14-dione (3) following this approach is presented.

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