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The first total synthesis of (+/-)-ingenol.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2002 Aug 21; Vol. 124 (33), pp. 9726-8. - Publication Year :
- 2002
-
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 Delta13,14 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-6alpha hydroxymethyl group as the sole handle for oxidation of seven contiguous carbon centers.
Details
- Language :
- English
- ISSN :
- 0002-7863
- Volume :
- 124
- Issue :
- 33
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 12175229
- Full Text :
- https://doi.org/10.1021/ja026600a