Synthesis of fused-ring nicotine derivatives from (S)-nicotine.
The synthesis of novel fused-ring bicyclic (4-6) and tricyclic (7-10) nicotine derivatives from natural (S)-nicotine are described. Enantiopure bicyclic dioxino, dihydrofuro, and dihydropyranol nicotine derivatives as well as tricylic benzofuro and benzopyran derivatives were synthesized from simple alkoxy or halonicotine intermediates. Attempts to synthesize furonicotines (11, 12) resulted in formation of the furonicotine dimers 42 and 49.
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Pauline W
PW
Ondachi
Daniel L
DL
Comins
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004147:Dioxins / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009538:Nicotine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004147:Dioxins; D009538:Nicotine