Parvifloron F (1), an abietane diterpene isolated from Plectranthus parviflorous, features a conjugated o-hydroxy-p-quinone methide and an ester group at ring-A. It has been reported to show anti-oxidative activity as well as antibacterial activity against Listeria monocytogenes and Mycobacterium tuberculosis. Our preliminary study revealed that 1 exhibited potent antiproliferative activity against several human tumor cell lines, including a multidrug-resistant cell line. Despite its attractive bioactivities, synthetic studies oriented toward structure-activity relationship (SAR) determination have not been reported. We will present the first total synthesis of 1 starting from commercially available veratrole. The antiproliferative activity of the prepared derivatives, including synthetic intermediates, and SAR studies will also be discussed.

Total synthesis of bioactive diterpene, parvifloron F

254th National Meeting (2017)

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