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

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

doi:10.1039/c8cc05697h

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

Izuru Tsuchimochi, Yuta Kitamura, Hiroshi Aoyama, Shuji Akai, Keiyou Nakai, Takehiko Yoshimitsu

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	9893-9896
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	71
DOIs	https://doi.org/10.1039/c8cc05697h
Publication status	Published - 2018

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1039/c8cc05697h

Cite this

@article{f0ebdda541ec4919ab19ccd83c4fd09f,

title = "Total synthesis of (-)-agelastatin A: An SH2′ radical azidation strategy",

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.",

author = "Izuru Tsuchimochi and Yuta Kitamura and Hiroshi Aoyama and Shuji Akai and Keiyou Nakai and Takehiko Yoshimitsu",

year = "2018",

doi = "10.1039/c8cc05697h",

language = "English",

volume = "54",

pages = "9893--9896",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "71",

}

TY - JOUR

T1 - Total synthesis of (-)-agelastatin A

T2 - An SH2′ radical azidation strategy

AU - Tsuchimochi, Izuru

AU - Kitamura, Yuta

AU - Aoyama, Hiroshi

AU - Akai, Shuji

AU - Nakai, Keiyou

AU - Yoshimitsu, Takehiko

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85052748202&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85052748202&partnerID=8YFLogxK

U2 - 10.1039/c8cc05697h

DO - 10.1039/c8cc05697h

M3 - Article

C2 - 30083679

AN - SCOPUS:85052748202

SN - 1359-7345

VL - 54

SP - 9893

EP - 9896

JO - Chemical Communications

JF - Chemical Communications

IS - 71

ER -