title: Total synthesis of (+)-macquarimicin A.
abstract: The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)-C(3) geometry to be Z. The synthesis features a transannular Diels-Alder reaction, which constructed the tetracyclic framework stereoselectively, and a convergent and efficient synthetic pathway, which afforded (+)-macquarimicin A (1) in 27 steps (longest linear sequence) with 9.9% overall yield.
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Munakata
authors.forename: Hironori
authors.initials: H
authors.lastname: Katakai
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Ueki
authors.forename: Jun
authors.initials: J
authors.lastname: Kurosaka
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Takao
authors.forename: Kin-ichi
authors.initials: K
authors.lastname: Tadano
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis*; D008847:Micromonospora / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C094822:macquarimicin A