IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: asymmetric synthesis of (+)-luciduline.
[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.
Comins
D L
DL
Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA. daniel_comins@ncsu.edu
Brooks
C A
CA
al-awar
R S
RS
Goehring
R R
RR
D008352:Mannich Bases; D010946:Plants, Medicinal / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D008352:Mannich Bases; D011804:Quinolines; C410447:luciduline