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DOI: 10.1055/s-0028-1087698
Synthesis of ()-Psychotrimine
Contributor(s):Philip Kocienski, Zofia KomstaThe Scripps Research Institute, La Jolla, USA
Total Synthesis of ()-Psychotrimine
J. Am. Chem. Soc. 2008, 130: 10886-10887
Publication History
Publication Date:
19 February 2009 (online)
Key words
psychotrimine - Buchwald-Goldberg-Ullman reaction - palladium
Significance
Psychotrimine was isolated from a South African rainforest shrub Psychotria rostrata, belonging to the coffee family. This very concise and high-yielding synthesis features a unique, direct indole-aniline coupling (A → D). More than two gram of the target molecule was obtained in four relatively high-yielding steps.
Comment
The direct coupling of bromotrypt-amine derivative A with iodoaniline B afforded adduct D in a satisfactory yield. The Pd-catalyzed reaction of D with alkyne E resulted in F, which was next subjected to a chemoselective Buchwald-Goldberg-Ullman reaction that gave N-arylation product I. The subsequent treatment of I with Red-Al afforded the target molecule.