Total Synthesis of Sphingofungin F by Orthoamide-Type Overman Rearrangement of an Unsaturated Ester

被引：33

作者：

Tsuzaki, Shun ^{[1
]}

Usui, Shunme ^{[1
]}

Oishi, Hiroki ^{[1
]}

Yasushima, Daichi ^{[1
]}

Fukuyasu, Takahiro ^{[1
]}

Oishi, Takeshi ^{[2
]}

Sato, Takaaki ^{[1
]}

Chida, Noritaka ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

[2] Keio Univ, Sch Med, Kohoku Ku, Yokohama, Kanagawa 2238521, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 07期

关键词：

ALPHA-AMINO-ACID; ASYMMETRIC-SYNTHESIS; SPHINGOSINE; INHIBITORS; CASCADE; (-)-MORPHINE; LIGANDS; ECONOMY; POTENT;

D O I：

10.1021/acs.orglett.5b00475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. © 2015 American Chemical Society.

引用

页码：1704 / 1707

页数：4

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