6533b7d4fe1ef96bd1261d9a

RESEARCH PRODUCT

Stereoselective synthesis of polyoxygenated atisane-type diterpenoids

Consuelo AgullóIsmael NavarroAna C. CuñatAntonio Abad

subject

chemistry.chemical_classificationKetoneChemistryCyclopropanationStereochemistryOrganic ChemistryRegioselectivityBiochemistryTerpenechemistry.chemical_compoundIntramolecular forceDrug DiscoveryOrganic chemistryStereoselectivityDiazoDiels–Alder reaction

description

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.

yearjournalcountryeditionlanguage
2001-12-01Tetrahedron Letters
https://doi.org/10.1016/s0040-4039(01)01953-0