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A Novel Approach to Prezizaane Sesquiterpenes
Author(s) -
Goeke Andreas,
Mertl Daniel,
Brunner Gerhard
Publication year - 2004
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200490149
Subject(s) - chemistry , terpene , stereochemistry , computational biology , biology
Prezizaane sesquiterpenes are an olfactorily interesting class of tricyclic natural products, which occur in some precious perfumery raw materials. These compounds are biosynthetically derived from farnesyl pyrophosphate via cyclization, but some questions regarding the stereoselectivity of this process have not yet been answered. We discuss a novel and concise access to the tricyclic framework of these sesquiterpenes, as exemplified by the synthesis of (±)‐5 ‐epi‐ sesquithuriferone (5‐ epi ‐ 4 ).