Total synthesis of sphingofungin f by orthoamide-type Overman rearrangement of an unsaturated ester

Shun Tsuzaki, Shunme Usui, Hiroki Oishi, Daichi Yasushima, Takahiro Fukuyasu, Takeshi Oishi, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The total synthesis of sphingofungin F through the Overman rearrangement of an unsaturated ester, which is known to be an unsuitable substrate under standard conditions due to the competitive aza-Michael reaction, is described. The developed conditions enabled the ester to be compatible with the original Overman rearrangement, providing quick access to α,α-disubstituted amino acids by minimizing extra protecting group manipulations and redox reactions.

Original languageEnglish
Pages (from-to)1704-1707
Number of pages4
JournalOrganic Letters
Volume17
Issue number7
DOIs
Publication statusPublished - 2015 Apr 3

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esters
Esters
Michael reaction
Redox reactions
synthesis
Oxidation-Reduction
amino acids
manipulators
Amino Acids
Substrates
sphingofungin F

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Total synthesis of sphingofungin f by orthoamide-type Overman rearrangement of an unsaturated ester. / Tsuzaki, Shun; Usui, Shunme; Oishi, Hiroki; Yasushima, Daichi; Fukuyasu, Takahiro; Oishi, Takeshi; Satou, Takaaki; Chida, Noritaka.

In: Organic Letters, Vol. 17, No. 7, 03.04.2015, p. 1704-1707.

Research output: Contribution to journalArticle

Tsuzaki, Shun ; Usui, Shunme ; Oishi, Hiroki ; Yasushima, Daichi ; Fukuyasu, Takahiro ; Oishi, Takeshi ; Satou, Takaaki ; Chida, Noritaka. / Total synthesis of sphingofungin f by orthoamide-type Overman rearrangement of an unsaturated ester. In: Organic Letters. 2015 ; Vol. 17, No. 7. pp. 1704-1707.
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