Assembling the Methanoindene Cage of Phragmalin-Type Natural Products

Journal of Organic Chemistry 2023
Joseph Becica, Olavs Rāciņš, Marija Ivanova, Aigars Jirgensons

Phragmalin-type limonoids are highly complex natural products based on an unusual octahydro-1H-2,4-methanoindene cage. The absence of feasible routes to sufficiently functionalized methanoindene cage building blocks impedes the total synthesis of these natural products. We have developed a short and robust route to methanoindene cage compounds from the Hajos-Parrish ketone (HPK). Several stereoselective modifications of the HPK provided a substrate that underwent aldol reaction as a key step for the cage formation.

Keywords
Alcohols, Ketones, Molecular structure, Organic reactions, Pharmaceuticals
DOI
10.1021/acs.joc.3c00952
Hyperlink
https://pubs.acs.org/doi/10.1021/acs.joc.3c00952

Becica, J., Rāciņš, O., Ivanova, M., Jirgensons, A. Assembling the Methanoindene Cage of Phragmalin-Type Natural Products. Journal of Organic Chemistry, 2023, Vol. 88, No. 14, pp.10306-10309. ISSN 0022-3263. Available from: doi:10.1021/acs.joc.3c00952

Publication language
English (en)