title: Synthesis of (-)-muricatacin.
abstract: The synthesis of (-)-muricatacin starting from 1-bromododecane and 2-pentyn-1-ol is described. 2-Pentadecyn-1-ol (4), which was prepared from 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy alcohol 6 through a two-step reaction sequence, 6 being successively submitted to tosylation, iodination, chain extension with tert-butyl lithioacetate, and acid-catalyzed cyclization to give (-)-muricatacin (1a). Recrystallization afforded optically pure 1a.
authors.affiliation: Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, Sendai, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Makabe
authors.forename: A
authors.initials: A
authors.lastname: Tanaka
authors.forename: T
authors.initials: T
authors.lastname: Oritani
mesh_terms: D003460:Crystallization; D005663:Furans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D005663:Furans; C082488:muricatacin