The first total synthesis of (±)-ingenol

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Abstract

The first total synthesis of (±)-ingenol has been achieved. The key features of the synthesis include the use of a highly diastereoselective Michael reaction to fix the C-11 methyl stereochemistry and the incorporation of the dimethylcyclopropane via diastereoselective carbene addition to the Δ13,14 olefin. The intramolecular dioxenone photoaddition-fragmentation sequence leads to the establishment of the critical C-8/C-10 trans intrabridgehead stereochemistry, a central challenge in the synthesis of ingenanes. The completion of the synthesis proceeds using the C-6α hydroxymethyl group as the sole handle for oxidation of seven contiguous carbon centers. Copyright © 2002 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)9726-9728
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number33
DOIs
StatePublished - 21 Aug 2002