Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol.
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.
Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500 607, India.
T Vijai Kumar
TV
Reddy
B L A
BL
Prabhavathi Devi
R B N
RB
Prasad
M
M
Poornima
C
C
Ganesh Kumar
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002175:Candida / Q000187:drug effects; D007851:Dodecanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure
C495165:2-aminododecan-3-ol; D000935:Antifungal Agents; D007851:Dodecanol