title: Total synthesis of the proposed structure for pyragonicin.
abstract: [structure: see text] The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.
authors.affiliation: RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@postman.riken.go.jp
authors.forename: Shunya
authors.initials: S
authors.lastname: Takahashi
authors.forename: Narihito
authors.initials: N
authors.lastname: Ogawa
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
authors.forename: Tadashi
authors.initials: T
authors.lastname: Nakata
mesh_terms: D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry; D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D054378:Acetogenins; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; C509193:pyragonicin