Synthesis of 11-hydroxydrim-8(9)-en-7-one and 11,12-dihydroxydrim-8(9)-en-7-one from drim-8(9)-en-7-one |
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Authors: | P F Vlad D P Popa E C Gorincioi M N Coltsa G N Mironov |
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Institution: | (1) Institute of Chemistry, Academy of Sciences of Republic of Moldova, 3 str. Academiei, MD-2028 Chişinau, Republic of Moldova |
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Abstract: | A synthetic route to 11-hydroxydrim-8(9)-en-7-one and 11,12-hydroxydrim-8(9)-en-7-one, valuable key intermediates for the
preparation of naturally occurring biologically active drimanic sesquiterpenoids, starting from easily available drim-8(9)-en-7-one
was developed. 11-Hydroxydrim-8(9)-en-7-one was obtained by peracidic oxidation of the enol acetate of drim-8(9)-en-7-one.
11,12-Dihydroxydrim-8(9)-en-7-one was synthesized from drim-8(9)-en-7-one by two routes, namely, by a five-step procedurevia 11-hydroxydrim-8(9)-en-7-one and by bromination of drim-8(9)-en-7-one with NBS to give 11,12-dibromodrim-8(9)-en-7-one followed
by its acetoxylation and deacetylation.
Deceased
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 95–98, January, 2000. |
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Keywords: | drimanic sesquiterpenoids synthesis drim-8(9)-en-7-one 11-hydroxydrim-8(9)-en-7-one 11 12-dihydroxydrim-8(9)-en-7-one |
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