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

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Total synthesis of (−)-agelastatin A: an S_H2′ radical azidation strategy†

Izuru Tsuchimochi,^ab Yuta Kitamura,^b Hiroshi Aoyama,^b Shuji Akai,^b Keiyo Nakai^a and Takehiko Yoshimitsu*^a

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* Corresponding authors

^a 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
E-mail: yoshimit@okayama-u.ac.jp
Tel: +81-86-251-7930

^b Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan

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.

This article is part of the themed collection: Natural product synthesis

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Article information

DOI: https://doi.org/10.1039/C8CC05697H
Article type: Communication
Submitted: 14 Jul 2018
Accepted: 01 Aug 2018
First published: 07 Aug 2018

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Chem. Commun., 2018,54, 9893-9896

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

I. Tsuchimochi, Y. Kitamura, H. Aoyama, S. Akai, K. Nakai and T. Yoshimitsu, Chem. Commun., 2018, 54, 9893 DOI: 10.1039/C8CC05697H

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Chemical Communications