Synfacts 2007(10): 1019-1019  
DOI: 10.1055/s-2007-968944
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Butylcycloheptylprodigiosin

Contributor(s): Philip Kocienski, Indu Dager
J. T. Reeves*
Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, USA
Further Information

Publication History

Publication Date:
07 November 2007 (online)

Significance

Butylcycloheptylprodigiosin is isolated from a strain of Streptomyces sp. Y-42 also formed during the fermentation of mutant strains of Streptomyces. The synthesis features a novel method for the appendage of a pyrrole ring to a cycloalkenone and proceeds in 23% overall yield (five steps) versus 1.5% yield (16 steps) for a previous synthesis (A. Fürstner et al. Chem. Eur. J. 2007, 13, 1929).