Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope rearrangement.
Parallel effort: Stereodivergent parallel kinetic resolution of a racemic mixture of dienes using Davies' [Rh(2){(S)-dosp}(4)] or [Rh(2){(R)-dosp}(4)] catalysts promotes a tandem vinyl diazoacetate cyclopropanation/Cope rearrangement sequence to afford two diastereomeric, enantioenriched cycloheptadienes, which correspond to the natural antipodes of the title diterpenoids (see scheme).
Miller
Laura C
LC
Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.
Ndungu
J Maina
JM
Sarpong
Richmond
R
D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D004224:Diterpenes; C530546:cyanthiwigin F; C501253:cyanthiwigin U; C497675:cyathane; D012238:Rhodium