First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry.
[reaction: see text] By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
Yujiro
Y
Hayashi
Mitsuru
M
Shoji
Takasuke
T
Mukaiyama
Hiroaki
H
Gotoh
Shinpei
S
Yamaguchi
Munetaka
M
Nakata
Hideaki
H
Kakeya
Hiroyuki
H
Osada
D000935:Antifungal Agents / Q000138:chemical synthesis*; D001597:Benzylidene Compounds / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis; D013237:Stereoisomerism
D000935:Antifungal Agents; D001597:Benzylidene Compounds; D011760:Pyrrolidinones; C068886:synerazol