Enantioselective synthesis of (11E, 13S)-13-hydroxy-10-oxooctadecenoic acid, the cytotoxic principle of corn.
A brief and practical enantiomeric synthesis of the title compound has been developed. The salient features of the synthesis were: (i) preparation of the required chiron, 3-octyn-1-ol via a Candida rugosa lipasecatalyzed trans-acylation, (ii) use of easily accessible and inexpensive materials viz. 10-undecenoic acid and (iii) use of a simple reaction protocol.
Sharma
A
A
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai, India.
Chattopadhyay
S
S
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013229:Stearic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D003313:Zea mays / Q000737:chemistry*
C115508:13-hydroxy-10-oxooctadecenoic acid; D013229:Stearic Acids