6533b870fe1ef96bd12cfa30

RESEARCH PRODUCT

Syntheses of Oxygenated Spongiane Diterpenes from Carvone. Synthesis of Dorisenone C.

Ana C. CuñatConsuelo AgullóAntonio AbadAna Belen Garcı́a

subject

TerpeneCarvonechemistry.chemical_compoundDieneChemistryStereochemistryIntramolecular forceMoietyGeneral MedicineDiterpeneAdduct

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.

https://doi.org/10.1002/chin.200527173