Efforts toward the total synthesis of (+)-Cryptofolione employing a convergent synthetic strategy are presented. (+)-Cryptofolione was isolated from the crude extract of Cryptocarya conncina, a plant of the laurel family found in Brazil, and is known to be a G2 checkpoint inhibitor in human breast carcinoma MCF-7 cells. Structural features of Cryptofolione include a phenyl-substituted olefin, a 1,3-anti-diol subunit, and an α,β-unsaturated δ-lactone moiety. Highlights of the current synthetic method, include: two one-pot phosphate tethered-mediated sequential protocols, namely RCM/CM/H2 and allylic transposition/tether removal, to generate the linear portion of the bioactive molecule. An RCM strategy was explored to generate the α,β-unsaturated δ-lactone piece. By employing a strategy amenable to modification of the electrophilic subunit, it is possible to produce natural product analogs to profile both their reactivity and biological response. We thank the National Science foundation grant CHE-1560279 for their support

Progress toward the total synthesis of (+)-cryptofolione and development of natural product analogues

253rd National Meeting (2017)

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