A concise and fully selective synthesis of the ant venom alkaloid (3S,5R,8S,9S)-3-butyl-5-propyl-8-hydroxyindolizidine.
A seven-step synthesis of (3S,5R,8S,9S)-3-butyl-5-propyl-8-hydroxyindolizidine (2), an ant venom alkaloid isolated from Myrmicaria melanogaster, is disclosed with an overall yield of 28.9%. The key feature of the synthesis is the use of the iodocyclization for the introduction of the hydroxyl group of the 3-piperidinol. Remarkably, all the reaction steps proceeded with excellent chemo-, regio- and/or diastereoselectivities.
Lin
Geng-Jie
GJ
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.
Huang
Pei-Qiang
PQ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000862:Ant Venoms / Q000737:chemistry*; D018360:Crystallography, X-Ray; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
C546213:3-butyl-5-propyl-8-hydroxyindolizidine; D000470:Alkaloids; D000862:Ant Venoms; D054836:Indolizidines