Total synthesis of (±)-cytisine

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4201-4204

  O'Neill, Brian T ^a   Yohannes, Daniel ^a   Bundesmann, Mark W ^a   Arnold, Eric P ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AZOCINE DERIVATIVE; CYTISINE; NICOTINIC AGENT; QUINOLIZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AZOCINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NICOTINIC AGONISTS; QUINOLIZINES; STEREOISOMERISM;

EID: 0034727943     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0067538     Document Type: Article

References (30)

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27. We have thus far been unable to use the conditions of Miyaura to directly prepare the "boron pinacolate" via a related palladium-catalyzed process. Ishiyama, T.; Myrata, M.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447. We have confirmed that the stannane derived from 2 methoxy-6-bromopyridine is also an excellent substrate for Stille coupling, affording 8a in 40% yield.
28. Independent observations along similar lines have been reported with pyridyl inflates: Hitchcock, S. A.; Mayhugh, D. R.; Gregory, G. S. Tetrahedron Lett. 1995, 36, 9085-8. Modified Stille reaction of 6-methoxypyridyl-2-triflate and 7 afforded product 8a in only 23% yield.
29. For an alternative approach, see: Zoltewicz, J. A.; Cruskie, M. P., Jr. J. Org. Chem. 1995, 60, 3487-3493.
30. 3, DMF; 3. NaOMe, DMF; see Supporting Information).