Synfacts 2009(11): 1183-1183  
DOI: 10.1055/s-0029-1218029
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Kapakahines B and F

Contributor(s):Philip Kocienski
T. Newhouse, C. A. Lewis, P. S. Baran*
The Scripps Research Institute, La Jolla, USA
Enantiospecific Total Syntheses of Kapakahines B and F
J. Am. Chem. Soc.  2009,  131:  6360-6361  
Further Information

Publication History

Publication Date:
22 October 2009 (online)


Significance

Kapakahines are metabolites of the sponge Cribrochalina olemda. Kapakahine B has modest antileukemic activity but kapakahine F is inactive. A salient feature of this short and efficient synthesis is the in situ kinetic trapping of the α-carboline G which is in dynamic equilibrium with the pyrroloindoline F.

Comment

Cyclization of the amino acid F (participating atoms highlighted in red) gives a macro­cycle (not shown) in 6% yield together with the ­desired α-carboline G. All the steps leading up to H were performed on a gram scale.