Synlett 1999; 1999(S1): 1006-1008
DOI: 10.1055/s-1999-3121
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Stereoselective Entry to the Bicycle[4.3.0] Skeleton of Oplopanes Using a Transannular Cyclization Strategy

Guillermo Delgado* , Salvador Guzmán
  • *Instituto de Química de la Universidad Nacional Autónoma de México. Circuito Exterior, Ciudad Universitaria, Coyoacán 04510. México, D.F.; Fax +52(5)6 16 22 17; E-mail: delgado@servidor.unam.mx
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.