Novel 1,5-Diepoxide rearrangements

Abstract

The epoxidic function of 8β,9β-epoxy-9,11-secopodocarp-11-ene (1) was inert to lithium aluminium hydride but underwent extremely facile intramolecular opening by a suitably placed nucleophile. The structure of the cyclized products formed, some anomalous ¹H n.m.r, chemical shifts and the behaviour of the analogous 8,17-epoxy-14,15,16-trinorlabd-12-ene (14) system are described.