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Total synthesis of (-)-agelastatin A: an SH2' radical azidation strategy
Izuru Tsuchimochi1, Yuta Kitamura2, Hiroshi Aoyama2
1Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan. yoshimit@okayama-u.ac.jp and Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Chemical Communications (Cambridge, England)
|August 8, 2018
Abstract:
A reagent generated from TMSN3/KMnO4/BnEt3NCl was found to promote an SH2' radical azidation of a bromo silyl enol ether to furnish an azido silyl enol ether via olefin transposition. With the present azidation protocol, a new synthetic approach to agelastatin A, a potent antitumor marine alkaloid, has been established.