title: Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis.
abstract: The first total synthesis of extracellular factor, "Avenolide", in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the absolute configuration of avenolide as 4S,10R, and yielded important information on its structure-activity relationship.
authors: School of Pharmacy, Kitasato University, Tokyo, Japan.
authors: Miho
authors: M
authors: Uchida
authors: Satoshi
authors: S
authors: Takamatsu
authors: Shiho
authors: S
authors: Arima
authors: Kiyoko T
authors: KT
authors: Miyamoto
authors: Shigeru
authors: S
authors: Kitani
authors: Takuya
authors: T
authors: Nihira
authors: Haruo
authors: H
authors: Ikeda
authors: Tohru
authors: T
authors: Nagamitsu
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: C004511:butenolide; D015107:4-Butyrolactone