Stereocontrolled Total Synthesis of Sphingofungin E

被引：23

作者：

Ikeuchi, Kazutada ^{[1
]}

Hayashi, Moemi ^{[1
]}

Yamamoto, Tomohiro ^{[1
]}

Inai, Makoto ^{[1
]}

Asakawa, Tomohiro ^{[1
]}

Hamashima, Yoshitaka ^{[1
]}

Kan, Toshiyuki ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 30期

关键词：

Asymmetric synthesis; Olefination; Oxidation; Rearrangement; Amino acids; BENZYL PROTECTIVE GROUP; OXIDATION; IMMUNOSUPPRESSANT; HYDROGENOLYSIS; REARRANGEMENT; MYRIOCIN;

D O I：

10.1002/ejoc.201301065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe herein the asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3)(2).

引用

页码：6789 / 6792

页数：4

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