Synfacts 2011(3): 0247-0247  
DOI: 10.1055/s-0030-1259413
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Perophoramidine

Contributor(s): Steven V. Ley, Kimberley A. Roper
H. Wu, F. Xue, X. Xiao, Y. Qin*
Sichuan University, Chengdu, P. R. of China
Further Information

Publication History

Publication Date:
16 February 2011 (online)

Significance

(+)-Perophoramidine is an indole ­alkaloid isolated from Perophora namei with a complex multiring system, bisamidine functionality, and two vicinal quaternary centers. This is the first asymmetric synthesis with four racemic syntheses of perophoramidine or the related communesins previously published. The key step in this synthesis is the asymmetric hetero-Diels-Alder ­reaction controlled by a chiral auxiliary. This synthesis allowed the determination of the absolute configuration of the natural product.