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Published on: October 15, 2019
Assembling the Methanoindene Cage of Phragmalin-Type Natural Products
Joseph Becica1, Olavs Ra Ciņš1, Marija Ivanova1
1Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
Abstract:
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.
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