A novel approach to prezizaane sesquiterpenes.
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).
Goeke
Andreas
A
Givaudan Schweiz AG, Fragrance Research, Uberlandstrasse 138, CH-8600 Dübendorf. andreas.goeke@givaudan.com
Mertl
Daniel
D
Brunner
Gerhard
G
D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D011106:Polyisoprenyl Phosphates / Q000737:chemistry / Q000302:isolation & purification; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification*
D010936:Plant Extracts; D011106:Polyisoprenyl Phosphates; D012717:Sesquiterpenes; C004808:farnesyl pyrophosphate