55012-72-1Relevant articles and documents
Total synthesis of (±)-cis-5-hydroxycalamenene
Poon Ng, Po S.,Banerjee, Ajoy K.
, p. 2261 - 2268 (2008/09/21)
A total synthesis of (±)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-α-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (±)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation. Copyright Taylor & Francis Group, LLC.
Studies on aromatic sesquiterpenes. XII. Synthesis of (±)-cis-5-Hydroxycalamenene
Tanaka,Adachi
, p. 272 - 274 (2007/10/02)
Starting from o-cresol, (±)-cis-5-hydroxycalamenene was synthesized through 4-isopropyl-5-methoxy-6-methyl-1-tetralone as a key intermediate and identified with the natural compound spectroscopically.
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.