Synthesis of Nicolaioidesin C

H. Cong; D. Ledbetter; G. T. Rowe; J. P. Caradonna; J. A. Porco, Jr.

doi:10.1055/s-0028-1087236

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Synfacts 2009(1): 0013-0013
DOI: 10.1055/s-0028-1087236

Synthesis of Natural Products and Potential Drugs

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

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Publication History

Publication Date:
18 December 2008 (online)

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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.