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Stereoselective Total Synthesis of Nimbolide
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A stereoselective total synthesis of nimbolide has been achieved in a convergent, 11-step sequence from α-methyl-(R)-carvone. The strategy relied on a stereoselective palladium-catalyzed borylative Heck cyclization where the A-ring of the nimbolide core was constructed while simultaneously installing oxidation at C28. Selective manipulations delivered a fully decorated decalin moiety on large scale. Then, a stereoretentive etherification reaction brought together two fragments and forged the critical C–O bond with high selectivity. Finally, a regioselective radical cyclization and late-stage lactonization completed the total synthesis of nimbolide.
American Chemical Society (ACS)
Title: Stereoselective Total Synthesis of Nimbolide
Description:
A stereoselective total synthesis of nimbolide has been achieved in a convergent, 11-step sequence from α-methyl-(R)-carvone.
The strategy relied on a stereoselective palladium-catalyzed borylative Heck cyclization where the A-ring of the nimbolide core was constructed while simultaneously installing oxidation at C28.
Selective manipulations delivered a fully decorated decalin moiety on large scale.
Then, a stereoretentive etherification reaction brought together two fragments and forged the critical C–O bond with high selectivity.
Finally, a regioselective radical cyclization and late-stage lactonization completed the total synthesis of nimbolide.
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