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A Pauson-Khand approach to the synthesis of ingenol.

[reaction: see text] Pauson-Khand cyclization of dioxanone photoadduct 21 leads to the formation of a single product in good yield. However, retro-aldol fragmentation of the pentacyclic cyclopentenone 22 leads to the formation of 23, with cis C-8/C-10 intrabridgehead stereochemistry, unlike the target compound ingenol 1, which possesses C-8/C-10 trans intrabridgehead stereochemistry.[1]


  1. A Pauson-Khand approach to the synthesis of ingenol. Winkler, J.D., Lee, E.C., Nevels, L.I. Org. Lett. (2005) [Pubmed]
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