title: An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-lodobromoethylene as a novel two-carbon synthon.
abstract: [structure: see text] Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized from commercially available (E)-1-bromopropene, acetylene, and propynoic acid in five steps (longest linear sequence) in 30% overall yield and >96% stereoselectivity. The preparation of (E)-iodobromoethylene and its use in the Pd-catalyzed cross coupling are two of the novel aspects of the synthesis reported herein.
authors.affiliation: Herbert C. Brown Laboratories, Purdue University, West Lafayette, Indiana 47907, USA. negishi@purdue.edu
authors.forename: E
authors.initials: E
authors.lastname: Negishi
authors.forename: A
authors.initials: A
authors.lastname: Alimardanov
authors.forename: C
authors.initials: C
authors.lastname: Xu
mesh_terms: D000924:Anticholesteremic Agents / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000924:Anticholesteremic Agents; D007783:Lactones; C066799:xerulin