6533b822fe1ef96bd127cbd6

RESEARCH PRODUCT

Synthetic studies on the preparation of oxygenated spongiane diterpenes from carvone

Ana Belen Garcı́aAna C. CuñatConsuelo AgullóCarlos Giménez-saizAntonio Abad

subject

TerpeneCarvonechemistry.chemical_compoundchemistryStereochemistryIntramolecular forceOrganic ChemistryDrug DiscoveryOrganic chemistryBiochemistryDiels–Alder reactionAdduct

description

Abstract The paper describes a new diastereoselective approach to oxygenated spongiane diterpenes functionally related to natural dorisenones. The strategy followed for the preparation of the spongiane framework, a B→AB→ABC→ABCD approach, is based on the preparation of epoxydecalone 11 (AB rings) from R-(−)-carvone, followed by an intramolecular Diels–Alder reaction for the construction of the C ring (compound 26 ). Further manipulation of the Diels–Alder adduct functionality allows the completion of the spongiane framework and the elaboration of several oxygenated spongiane-type compounds. The structures of two compounds 27 and 31 , has been established by single-crystal X-ray crystallography.

yearjournalcountryeditionlanguage
2003-11-01Tetrahedron
https://doi.org/10.1016/j.tet.2003.10.017