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Synthesis of oxygenated spongiane-type diterpenoids from carvone

✍ Scribed by Antonio Abad; Consuelo Agulló; Ana C. Cuñat; Ana Belen Garcı́a

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
176 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new diastereoselective approach to oxygenated spongiane diterpenes starting from (R)-(-)-carvone is described. The carvone is incorporated as the B ring in the final spongiane framework using a BABABCABCD approach, which involves an intramolecular Diels-Alder reaction and the regioselective ring-opening of a dihydrofuran ring as key synthetic steps. The structure of the key intermediate in this approach has been verified by X-ray crystallography.

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Stereoselective synthesis of polyoxygena
Stereoselective synthesis of polyoxygenated atisane-type diterpenoids
✍ Antonio Abad; Consuelo Agulló; Ana C Cuñat; Ismael Navarro 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 79 KB

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 cleava