title: Total synthesis of the antitumor acetogenin mosin B: desymmetrization approach to the stereodivergent synthesis of threo/trans/erythro-type acetogenins.
abstract: A total synthesis of the threo/trans/erythro-type acetogenin mosin B and one of its diastereomers has been achieved. The carbon skeleton is assembled in a convergent fashion from two segments (a THF ring segment and a gamma-lactone segment) through the Nozaki-Hiyama-Kishi reaction. The THF ring segment was stereoselectively constructed by a stereodivergent synthesis starting from a common intermediate (4-cyclohexene-1,2-diol) based on a desymmetrization strategy. The gamma-lactone segment was synthesized by coupling a triflate and a chiral alpha-sulfenyl gamma-lactone. By virtue of these synthetic results, we suggest that the absolute configuration of natural mosin B is 1 a. Antiproliferative effects of 1 a and 1 b were also investigated.
authors.affiliation: Graduate School of Pharmaceutical Sciences Osaka University, 1-6 Yamadaoka, Suita Osaka 565-0871, Japan.
authors.forename: Naoyoshi
authors.initials: N
authors.lastname: Maezaki
authors.forename: Naoto
authors.initials: N
authors.lastname: Kojima
authors.forename: Atsunobu
authors.initials: A
authors.lastname: Sakamoto
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Tominaga
authors.forename: Chuzo
authors.initials: C
authors.lastname: Iwata
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
authors.forename: Morito
authors.initials: M
authors.lastname: Monden
authors.forename: Bazarragchaa
authors.initials: B
authors.lastname: Damdinsuren
authors.forename: Shoji
authors.initials: S
authors.lastname: Nakamori
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010190:Pancreatic Neoplasms / Q000473:pathology; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C107769:mosin B