Total synthesis of broussonetine F

The orthoamide overman rearrangement of an allylic diol

Naoto Hama, Toshihiro Aoki, Shohei Miwa, Miki Yamazaki, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A first total synthesis of broussonetine F from diethyl l-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

Original languageEnglish
Pages (from-to)616-619
Number of pages4
JournalOrganic Letters
Volume13
Issue number4
DOIs
Publication statusPublished - 2011 Feb 18

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Amino Alcohols
synthesis
alcohols
diethyl tartrate
broussonetine F
allyl alcohol
tartaric acid

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Total synthesis of broussonetine F : The orthoamide overman rearrangement of an allylic diol. / Hama, Naoto; Aoki, Toshihiro; Miwa, Shohei; Yamazaki, Miki; Satou, Takaaki; Chida, Noritaka.

In: Organic Letters, Vol. 13, No. 4, 18.02.2011, p. 616-619.

Research output: Contribution to journalArticle

Hama, Naoto ; Aoki, Toshihiro ; Miwa, Shohei ; Yamazaki, Miki ; Satou, Takaaki ; Chida, Noritaka. / Total synthesis of broussonetine F : The orthoamide overman rearrangement of an allylic diol. In: Organic Letters. 2011 ; Vol. 13, No. 4. pp. 616-619.
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