Total synthesis of (+)-muconin.
(+)-Muconin (1), isolated from the leaves of Rollinia mucosa (Jacq.) Baill. (Annonaceae), is a sequential THF/THP-possessing acetogenin that exhibits potent and selective in vitro cytotoxicity toward pancreatic and breast tumor cell lines. In this study, a new route was established for obtaining (+)-muconin (1) starting with (-)-muricatacin (2), a compound recently synthesized via the novel alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofuran.
Yoshimitsu
Takehiko
T
Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. takey@my-pharm.ac.jp
Makino
Toshiyuki
T
Nagaoka
Hiroto
H
D054378:Acetogenins; D000478:Alkylation; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D018515:Plant Leaves / Q000737:chemistry; D031045:Rollinia / Q000737:chemistry*; D013237:Stereoisomerism
D054378:Acetogenins; D000972:Antineoplastic Agents, Phytogenic; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; D017646:Organosilicon Compounds; C485515:muconin; C082488:muricatacin