Total Synthesis of (±)-Cis-5-Hydroxycalamenene

Abstract

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.

Keywords:

• (±)-cis-5-hydroxycalamenene
• Grignard reaction
• 5-methoxy-α-tetralone
• Terpene

ACKNOWLEDGMENT

We thank LOCTI for partial financial support.