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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Parallel kinetic resolution approach to the cyathane and cyanthiwigin diterpenes using a cyclopropanation/Cope
Laura C Miller1, J Maina Ndungu, Richmond Sarpong
1Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.
Abstract:
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).
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