A Highly Stereoselective Asymmetric Synthesis of (−)-Lobeline and (−)-Sedamine

• Published in: Journal of organic chemistry Vol. 67; no. 26; pp. 9192 - 9199
• Main Authors: Felpin, François-Xavier, Lebreton, Jacques
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 27.12.2002; Amer Chemical Soc
• Subjects: Alkaloids - analysis; Alkaloids - chemical synthesis; Alkaloids - chemistry; Catalysis; Chemistry; Chemistry, Organic; Chemistry, Organic - methods; Chromatography, High Pressure Liquid; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Lobelia - chemistry; Lobeline - analysis; Lobeline - chemical synthesis; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Organic chemistry; Physical Sciences; Piperidines - analysis; Piperidines - chemical synthesis; Plants, Medicinal - chemistry; Preparations and properties; Science & Technology; Stereoisomerism; ALPHA-SUBSTITUTED PIPERIDINES; CATALYZED EPOXIDATIONS; SEDUM ALKALOIDS; HOMOALLYLIC ALCOHOLS; CHIRAL SYNTHESIS; ENANTIOSELECTIVE ALLYLTITANATION; ALDEHYDES; EN-ROUTE; STEREOCONTROLLED SYNTHESIS; SPONGISTATIN 1; Nitrogen heterocycle; Boration; Benzaldehyde; Alcohol; Aldehyde; Tricyclic compound; Ketone; Allylation; Chemical reduction; Stereoselectivity; Alkaloid; Cyclization; Asymmetric synthesis; Epoxide; Aromatic compound; Chemical synthesis; Enantiomer(-)
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo020501y

A highly stereoselective asymmetric synthesis of (−)-sedamine and (−)-lobeline is described from benzaldehyde in 16 and 17 steps with an overall yield of 20% and 14%, respectively. The key intermediate syn-3,4-epoxyalcohol was prepared in a highly diastereomeric fashion (>99% ee, dr) and served as a common intermediate for both alkaloids.