Journal of the American Chemical Society

Total synthesis of (+)-jatrophone.

Q Han, DF Wiemer

Index: Han, Qi; Wiemer, David F. Journal of the American Chemical Society, 1992 , vol. 114, # 20 p. 7692 - 7697

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Citation Number: 55

Abstract

Abstract: The first total synthesis of optically active (+)-jatrophone is described. A convergent sequence provides the natural enantiomer in just 12 steps from (R)-(+)-3-methyladipic acid. Key steps include formation of the jatrophone C-ring through a Wadsworth-Homer-Emmons variant, a Pd-catalyzed cross-coupling that incorporates the CSX 6 double bond with the required 2-stereochemistry, and formation of the macrocycle by condensation of an ...