Hypercalin C is a dearomatized isoprenylated phloroglucinol (DIP) isolated from the aerial parts of Hypericum calycinum L. It has been shown to be more potent than current colon cancer therapies, displaying an ED50 value of 0.78 �M against Co-115 HeLa cell line. The synthesis involves a practical, multi-gram sequence to access a versatile bicyclic �-lactone from (R)-carvone. The key transformation employs a diastereoselective nucleophile catalyzed aldol-lactonization (NCAL) process (dr >19:1) for the generation of the desired bicyclic �-lactone. Subsequent steps involve coupling of the �-lactone with an aromatic moiety and a late stage ortho-Claisen rearrangement to establish the dearomatized natural product. Studies toward the enantioselective synthesis of (+)-hypercalin C will be presented.

Enantioselective synthesis of (+)-hypercalin C

243rd National Meeting (2012)

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