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Synfacts 2006(12): 1198-1198  
DOI: 10.1055/s-2006-955590
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (S)-Brevicolline

Contributor(s): Philip Kocienski, Fiona Black
F. F. Wagner, D. L. Comins*
North Carolina State University, Raleigh, USA
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

The β-carboline alkaloid (S)-Brevicolline is synthesized in six steps from (S)-nicotine. Regioselective ortho-directed lithiation procedures gave a trisubstituted (S)-nicotine derivative which was used in a Suzuki coupling and intramolecular Buchwald amination to complete the synthesis.