Asymmetric total synthesis of (-)-panacene and correction of its relative configuration.
[reaction: see text] The first synthesis of (-)-panacene has been accomplished in concise, highly stereoselective fashion from commercially available 2-methoxy-6-methylbenzoic acid (15 steps, 8.3% overall yield). The synthesis unambiguously establishes the correct relative and absolute configuration of panacene, and demonstrates the serviceability of Pd(II)-mediated tandem intramolecular alkoxycarbonylation-lactonization for the expedient assembly of its tricyclic core, and the dual role of asymmetric alkynylation as an initial source of chirality and as a powerful tool for manipulating diastereoselectivity.
Boukouvalas
John
J
Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca
Pouliot
Martin
M
Robichaud
Joël
J
MacNeil
Stephen
S
Snieckus
Victor
V
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001048:Aplysia / Q000737:chemistry; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D006842:Hydrocarbons, Brominated; C519981:panacene; D010165:Palladium