IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: asymmetric synthesis of (+)-luciduline |
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| Authors: | Comins D L Brooks C A al-awar R S Goehring R R |
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| Institution: | Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA. daniel_comins@ncsu.edu |
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| Abstract: | formula: see text] The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished. Key steps include an IMDA reaction of a chiral dihydropyridine, a subsequent retro-Mannich ring opening, and a novel cationic reductive cyclization reaction. |
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