Determination of absolute structure of (−)-oudemansin b

✍ Scribed by Hiroyuki Akita; Hiroko Matsukura; Takeshi Oishil

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 268 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85221-1

✦ Synopsis

Oudemansin B (1) synthesized from (ZR,3S)-2,3-epoxybutyrate 2, based on microbial asymmetric r$duction of ketone was proved to be identical with natural oudemansin B (l), which established that the absolute configuration of j_ is 9S, 10s. Oudemansin B (l_) is an antibiotics isolated from mycelial cultures of Xerula melanotricha and inhibits the growth of a wide variety of saprophytic and phytopathogenic fungi at. very low concentrati0n.l) The structure has been deduced by spectroscopic methods and recently s n--V C9-OMe, C,O-Me structure has been confirmed by the synthesis of (+)-!, by Kallmerten et al.2 However, the absolute configurations of these two chiral centers are remained unknown. We now report that the absolute structure of !, was established as 9S, 10s by the total synthesis starting from chiral intermediate of known absolute structure.