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Synlett 1999; 1999(S1): 1006-1008
DOI: 10.1055/s-1999-3121
DOI: 10.1055/s-1999-3121
letter
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Stereoselective Entry to the Bicycle[4.3.0] Skeleton of Oplopanes Using a Transannular Cyclization Strategy
Further Information
Publication History
Publication Date:
31 December 1999 (online)
Treatment of budlein B with acid gave a H-4β,H-9α-oplopane via lactone cleavage, allylic rearrangement, transannular cyclization and pinacol-type rearrangement. This transformation is stereochemically complementary to that of schkuhriolide, which produces an H-4α,H-9β-oplopane.
oplopanes - sesquiterpenes - cyclization - rearrangement - stereoselectivity