6533b860fe1ef96bd12c2db8

RESEARCH PRODUCT

Syntheses of oxygenated spongiane diterpenes from carvone. Synthesis of dorisenone C

Ana Belen Garcı́aAna C. CuñatAntonio AbadConsuelo Agulló

subject

CarvoneDieneStereochemistryOrganic ChemistryBiochemistryAdductTerpenechemistry.chemical_compoundchemistryIntramolecular forceDrug DiscoveryMoietyOrganic chemistryDiterpeneDiels–Alder reaction

description

Abstract The synthesis of dorisenone C, a representative member of the spongiane-type diterpene family, is described. The synthesis follows a B→AB→ABC→ABCD approach and is based on the initial preparation of the previously known hydroxy-aldehyde 14 (AB rings) from R -(−)-carvone, followed by an intramolecular Diels–Alder reaction between an oxygenated diene moiety and an acetylenic dienophile for the construction of the C ring (compound 22 ), and adequate manipulation of the Diels–Alder adduct functionality for completion of the spongiane framework.

yearjournalcountryeditionlanguage
2005-02-01Tetrahedron
https://doi.org/10.1016/j.tet.2005.01.012