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

doi:10.1021/acs.orglett.5b00475

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 journal › Article › peer-review

29 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 language	English
Pages (from-to)	1704-1707
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.5b00475
Publication status	Published - 2015 Apr 3

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5b00475

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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.",

author = "Shun Tsuzaki and Shunme Usui and Hiroki Oishi and Daichi Yasushima and Takahiro Fukuyasu and Takeshi Oishi and Takaaki Sato and Noritaka Chida",

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T1 - Total synthesis of sphingofungin f by orthoamide-type Overman rearrangement of an unsaturated ester

AU - Tsuzaki, Shun

AU - Usui, Shunme

AU - Oishi, Hiroki

AU - Yasushima, Daichi

AU - Fukuyasu, Takahiro

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2015/4/3

Y1 - 2015/4/3

N2 - 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.

AB - 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.

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JO - Organic Letters

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

Abstract

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