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

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,...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (71), p.9893-9896
Main Authors: Tsuchimochi, Izuru, Kitamura, Yuta, Aoyama, Hiroshi, Akai, Shuji, Nakai, Keiyo, Yoshimitsu, Takehiko
Format: Article
Language:English
Subjects:
Potassium permanganate
Reagents
Online Access:Get full text
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc05697h