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Synfacts 2008(7): 0668-0668  
DOI: 10.1055/s-2008-1077868
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-WIN 64821 and (-)-Ditryptophenaline

Contributor(s): Philip Kocienski, Zofia Komsta
M. Movassaghi*, M. A. Schmidt, J. A. Ashenhurst
Massachusetts Institute of Technology, Cambridge, USA
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Publikationsverlauf

Publikationsdatum:
20. Juni 2008 (online)

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Significance

(+)-WIN 64821 and (-)-ditryptophen­aline are secondary metabolites of Aspergillus flavus. (+)-WIN 64821 is a potential submicromole­cular inhibitor of the human neurokinin 1 and cholecystokinin B receptors. The (-)-ditryptophen­aline exhibits weaker antagonistic effects. A concise and elegant synthesis from commercially available amino acid derivatives is presented. The key intermediates C, D and E were prepared on a gram scale.