title: Synthesis of all possible isomers corresponding to the proposed structure of montanacin E, and their antitumor activity.
abstract: Total synthesis of 4 and its three diastereomers is described. The key steps involve stereoselective formation of the tetrahydrofuran ring by a cascade cyclization of hydroxy tosylate 7 and an intermolecular cross metathesis between a tetrahydrofuran 5 and a gamma-lactone 6. Spectroscopic data of 4 and biosynthetic hypothesis strongly suggest it to be montanacin E. Inhibitory activities of 4 and its isomers against six human solid tumor cell lines were also evaluated.
authors: RIKEN, Wako, Saitama 351-0198, Japan. shunyat@riken.jp
authors: Shunya
authors: S
authors: Takahashi
authors: Ryotaro
authors: R
authors: Takahashi
authors: Yayoi
authors: Y
authors: Hongo
authors: Hiroyuki
authors: H
authors: Koshino
authors: Kazunori
authors: K
authors: Yamaguchi
authors: Taeko
authors: T
authors: Miyagi
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001156:Artemia / Q000187:drug effects; D045744:Cell Line, Tumor; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D006801:Humans; D020128:Inhibitory Concentration 50; D007536:Isomerism
chemical_list: D000970:Antineoplastic Agents; D005663:Furans; C552380:montanacin E