IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: Asymmetric synthesis of (+)-luciduline

Organic Letters

Volumn 1, Issue 2, 1999, Pages 229-231

  Comins, Daniel L ^a   Brooks, Clinton A ^a   Al Awar, Rima S ^a   Goehring, R Richard ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LUCIDULINE; MANNICH BASE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS;

MANNICH BASES; PLANTS, MEDICINAL; QUINOLINES; STEREOISOMERISM;

EID: 0033614872     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990028j     Document Type: Article

References (16)

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11. The (+)-and (-)-TCC alcohols are available from Aldrich Chemical Co.
12. The yield is for diastereomerically pure 8 isolated by radial preparative layer chromatography. The stereoselectivity ranged from 85 to 90%.
13. Furukawa, J.; Morisaki, N.; Kobayashi, H.; Iwasaki, S.; Nozoe, S.; Okuda, S. Chem. Pharm. Bull. 1985, 33, 440.
14. Onyl a single Diels-Alder product was observed. For model studies on related IMDA reactions and subsequent ring opening, see: Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1992, 57, 4098.
15. Rosenberg, S. H.; Spina, K. P.; Condon, S. L.; Polakowski, J.; Yao, Z.; Kovar, P.; Stein, H. H.; Cohen, J.; Barlow, J. L.; Klinghofer, V.; Egan, D. A.; Tricarico, K. A.; Perun, T. J.; Baker, W. R.; Kleinen, H. D. J. Med. Chem. 1993, 36, 460.
16. 13C NMR spectra and elemental analysis or high-resolution mass spectra.