title: Two-component method to enantiopure quinolizidinones and Indolizidinones. Total synthesis of (-)-lasubine II.
abstract: The reaction of iodides 1 and enantiopure beta-amino esters 2 mediated by potassium carbonate in acetonitrile at 65 degrees C provides quinolizidinones or indolizidinones 3, together with piperidines or pyrrolidines 4. Hydrolysis of 4 to the corresponding carboxylic acids followed by treatment of acetic anhydride/triethylamine gives 3 in high yields. Using 3a as a key intermediate, (-)-lasubine II is synthesized in four steps. [reaction: see text]
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
authors.forename: D
authors.initials: D
authors.lastname: Ma
authors.forename: W
authors.initials: W
authors.lastname: Zhu
mesh_terms: D007212:Indolizines / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007212:Indolizines; D011807:Quinolizines; C414385:lasubin I