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 Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

21 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

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Total synthesis of sphingofungin f by orthoamide-type Overman rearrangement of an unsaturated ester'. Together they form a unique fingerprint.

Cite this