Title of article
Stereoselective synthesis of polyoxygenated atisane-type diterpenoids
Author/Authors
Abad، نويسنده , , Antonio and Agullَ، نويسنده , , Consuelo and Cuٌat، نويسنده , , Ana and Garcيa Navarro، نويسنده , , Ismael، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2001
Pages
4
From page
8965
To page
8968
Abstract
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.
Keywords
Cyclopropanation , radical cleavage , Diels–Alder reaction , terpene , carvone , atisane
Journal title
Tetrahedron Letters
Serial Year
2001
Journal title
Tetrahedron Letters
Record number
1648723
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