82054-01-1Relevant articles and documents
Studies in Terpenoids: Part LV - Synthesis of 5-Hydroxycalamenene, a Phenolic Sesquiterpene from Bazzania tricrenata
Sangaiah, R.,Rao, G. S. Krishna
, p. 13 - 15 (2007/10/02)
Fries rearrangement of o-cresyl isobutyrate (IV) gives the o-hydroxyketone (V).Dehydration and saponification of the Reformatsky reaction product of the methoxyketone (VI) with ethyl bromoacetate affords the unsaturated acid mixture (VII).The saturated aryl methylpentanoic acid (VIII) derived from VII is reacted with ethyllithium to give the ketone (IX).The secondary alcohol (X) obtained from IX is cyclodehydrated and demethylated in one step to give 5-hydroxycalamenene (I) which is produced stepwise also from X via the methoxytetralin (XI) obtained by PPA treatment.