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
收藏
页码：4678 / 4680
页数：3
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