Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation.
The cedrene carbon skeleton was rapidly assembled from a simple monocyclic precursor by the strategic use of a high yielding intramolecular Khand cyclization reaction. Further synthetic manipulations provided a concise formal total synthesis of alpha- and beta-cedrene. Reaction: see text.
Kerr
W J
WJ
Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, U.K. w.kerr@strath.ac.uk
McLaughlin
M
M
Morrison
A J
AJ
Pauson
P L
PL
D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis; D007536:Isomerism; D018653:Juniperus / Q000737:chemistry; D010938:Plant Oils / Q000138:chemical synthesis*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D010938:Plant Oils; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C000393:cedrene