A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-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.
A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-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.
Total Synthesis of (±)-<b> <i>Cis</i> </b>-5-Hydroxycalamenene
作者:Po S. Poon Ng、Ajoy K. Banerjee
DOI:10.1080/00397910802026204
日期:2008.6.20
A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-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.