Anion relay chemistry extended. Synthesis of a gorgonian sesquiterpene.
Extension of anion relay chemistry (ARC) beyond the area of dithianes has been achieved by the design of two effective ARC linchpins capable of three- and four-component couplings. To showcase the ARC tactic in natural product synthesis, a cytotoxic gorgonian linear sesquiterpene was constructed, and the absolute configuration assigned via the Kakisawa/Mosher method. The synthesis proceeded in five steps with an overall yield of 22%.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Kim
Dae-Shik
DS
Xian
Ming
M
D000838:Anions; D001688:Biological Products / Q000138:chemical synthesis; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000838:Anions; D001688:Biological Products; D012717:Sesquiterpenes