title: Formal total synthesis of lactimidomycin.
abstract: A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.
authors.affiliation: Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University , Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Nagasawa
authors.forename: Shigefumi
authors.initials: S
authors.lastname: Kuwahara
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D018942:Macrolides; D010881:Piperidones; D061065:Polyketides; C077633:lactimidomycin