Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol

被引：6

作者：

Reddy, T. Vijai Kumar ^{[1
]}

Devi, B. L. A. Prabhavathi ^{[1
]}

Prasad, R. B. N. ^{[1
]}

Poornima, M. ^{[2
]}

Kumar, C. Ganesh ^{[2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Ctr Lipid Res, Hyderabad 500607, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Biol Chem Lab, Hyderabad 500607, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 14期

关键词：

10-Undecenoic acid; Wittig reaction; Sharpless asymmetric epoxidation; Miyashita's azidolysis; Antifungal; SPONGE OCEANAPIA-PHILLIPENSIS; MISCELLANEOUS MECHANISMS; ANTIVIRAL ACTIVITIES; MARINE PHARMACOLOGY; NERVOUS SYSTEMS; SEX-PHEROMONE; EPOXIDE; ANTIBACTERIAL; ANTICOAGULANT; BIOSYNTHESIS;

D O I：

10.1016/j.bmcl.2012.05.082

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We report the total synthesis of (2S,3R)-2-aminododecan-3-ol has been achieved starting from commercially available 10-undecenoic acid. The key steps involved are Sharpless asymmetric epoxidation, Miyashita's boron-directed C-2 regioselective azidolysis, generated the asymmetric centers and in situ detosylation and reduction of azido tosylate. The antifungal activity of the synthesized (2S,3R)-2-aminododecan-3-ol was evaluated on several Candida strains and was comparable to miconazole, a standard drug (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4678 / 4680

页数：3

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