Enantiocontrolled preparation of indolizidines: synthesis of (-)-2-epilentiginosine and (+)-lentiginosine.
A highly stereoselective approach to (-)-2-epilentiginosine and (+)-lentiginosine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether. The two naturally occurring indolizidines are each obtained enantioselectively (> or = 99:1) in ca. 8.5% overall yield.
Rasmussen
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MO
Université Joseph Fourier de Grenoble, LEDSS, Chimie Recherche (LEDSS), 38041 Grenoble Cedex, France.
Delair
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Greene
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D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D000970:Antineoplastic Agents; D007212:Indolizines; C063984:lentiginosine; D006026:Glycoside Hydrolases; C434292:2-epilentiginosine