6533b85dfe1ef96bd12bdc19

RESEARCH PRODUCT

A unified synthetic approach to trachylobane-, beyerane-, atisane- and kaurane-type diterpenes

Consuelo AgullóIgnacio De Alfonso MarzalAntonio GrisAntonio AbadAna C. CuñatIsmael Navarro

subject

chemistry.chemical_classificationKetoneCyclopropanationStereochemistryOrganic ChemistryRegioselectivityRing (chemistry)BiochemistryCyclopropanechemistry.chemical_compoundchemistryDrug DiscoveryOrganic chemistryMoietyDiazoDiterpene

description

A general synthetic approach to the polycyclic carbon skeleton of biogenetically related trachylobane, beyerane, atisane, and kaurane diterpenes from carvone is described. The skeleton of these diterpenes is prepared from a common intermediate, that is, 25, readily prepared from carvone using an IMDA reaction and an intramolecular diazo ketone cyclopropanation of an unsaturated ketone as key steps. The tetracyclic diterpene ring systems are obtained from this key trachylobane-type intermediate through the regioselective reductive cleavage of the cyclopropane ring, after adequate modification of the functionalization around the tricyclo[3.2.1.02,7]octane moiety.

yearjournalcountryeditionlanguage
2006-04-01Tetrahedron
https://doi.org/10.1016/j.tet.2006.01.062