The synthesis of austrodoral (1), a marine nor-sesquiterpene that contains a unique bicyclic skeleton, has been achieved. The synthetic strategy is based on the ring contraction of a suitable optically active drimanic epoxy derivative, obtained from commercially available (+)-sclareolide (4). Fluorosulfonic acid was found to promote the ring contraction efficiently. The nor-sesquiterpene hydrocarbon 13, a key intermediate in the synthesis of sesquiterpene hydroquinones, has also been prepared in optically active form.
Further synthetic studies towards the austrodorane skeleton: synthesis of austrodoral.
Carbone M;Cimino G
2005
Abstract
The synthesis of austrodoral (1), a marine nor-sesquiterpene that contains a unique bicyclic skeleton, has been achieved. The synthetic strategy is based on the ring contraction of a suitable optically active drimanic epoxy derivative, obtained from commercially available (+)-sclareolide (4). Fluorosulfonic acid was found to promote the ring contraction efficiently. The nor-sesquiterpene hydrocarbon 13, a key intermediate in the synthesis of sesquiterpene hydroquinones, has also been prepared in optically active form.File in questo prodotto:
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