Synfacts 2009(1): 0013-0013  
DOI: 10.1055/s-0028-1087236
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Nicolaioidesin C

Contributor(s): Philip Kocienski
H. Cong, D. Ledbetter, G. T. Rowe, J. P. Caradonna, J. A. Porco, Jr.*
Boston University, USA
Further Information

Publication History

Publication Date:
18 December 2008 (online)

Significance

The synthesis of nicolaioidesin C exemplifies a general procedure for effecting ­electron transfer initiated Diels-Alder reactions of 2-hydroxychalcones with 1,3-dienes. The procedure uses either Co(I) or BH4 - as the electron transfer agent in the presence of ZnI2 as a bidentate Lewis acid. The mechanism proposed accounts for the formation of a single trans dia­stereoisomer.