Stereoselective total synthesis of amicoumacin C

被引：13

作者：

Suzuki, Tomomi ^{[1
]}

Nagasawa, Tomohiro ^{[1
]}

Enomoto, Masaru ^{[2
]}

Kuwahara, Shigefumi ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Agr Sci, Lab Appl Bioorgan Chem, Aoba Ku, Sendai, Miyagi 9818555, Japan

[2] Natl Inst Adv Ind Sci & Technol, Bioprod Res Inst, Sapporo, Hokkaido 0628517, Japan

来源：

TETRAHEDRON | 2015年 / 71卷 / 13期

关键词：

Amicoumacin; Isocoumarin; Diastereoselective reduction; Antibacterial; Total synthesis; BIOLOGICALLY-ACTIVE METABOLITES; BACTERIUM BACILLUS-SUBTILIS; MICROBIAL AGENT AI-77-B; GASTROPROTECTIVE SUBSTANCE; PUMILUS AI-77; ISOCOUMARIN; PRODUCTS; BACIPHELACIN; TRANSLATION; DERIVATIVES;

D O I：

10.1016/j.tet.2015.02.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantio- and diastereoselective total synthesis of amicoumacin C was achieved from L-phenylalanine in 17% overall yield through 13 steps via condensation between an amine and an acid segment. The amine segment was prepared from L-leucine in 42% yield by a 7-step sequence involving a diastereoselective reduction of an alpha-dibenzylamino ketone intermediate, while the acid segment was obtained from L-phenylalanine by using acidic hydrolysis of an acetonide-protected amide accompanied by concomitant lactonization as a key step. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1992 / 1997

页数：6

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