Total synthesis of (+)-benzastatin E via diastereoselective Grignard addition to 2-acylindoline.
[reaction: see text] A stereoselective total synthesis of (+)-benzastatin E (1) is described. The synthesis involves a diastereoselective Grignard addition to 2-acylindoline 2, which is derived from commercially available (S)-2-indolinecarboxylic acid (3). The unknown absolute configuration of (+)-1 is determined as (9S,10R).
Toda
Narihiro
N
Exploratory Chemistry Research Laboratories, Sankyo Co, Ltd, 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan.
Ori
Mayuko
M
Takami
Kazuko
K
Tago
Keiko
K
Kogen
Hiroshi
H
D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C473421:2-acylindoline; D001549:Benzamides; D007211:Indoles; C473420:benzastatin E