Total synthesis of (-)-agelastatin A: an SH2' radical azidation strategy

Izuru Tsuchimochi; Yuta Kitamura; Hiroshi Aoyama; Shuji Akai; Keiyo Nakai; Takehiko Yoshimitsu

doi:10.1039/c8cc05697h

Total synthesis of (-)-agelastatin A: an S_H2' radical azidation strategy

Chem Commun (Camb). 2018 Sep 14;54(71):9893-9896. doi: 10.1039/c8cc05697h. Epub 2018 Aug 7.

Authors

Izuru Tsuchimochi¹, Yuta Kitamura², Hiroshi Aoyama², Shuji Akai², Keiyo Nakai³, Takehiko Yoshimitsu³

Affiliations

¹ Division 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.
² Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
³ Division 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.

PMID: 30083679
DOI: 10.1039/c8cc05697h

Abstract

A reagent generated from TMSN₃/KMnO₄/BnEt₃NCl was found to promote an S_H2' 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.