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Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

2015; American Chemical Society; Volume: 78; Issue: 6 Linguagem: Inglês

10.1021/acs.jnatprod.5b00354

1520-6025

Andrew M. White, Gregory K. Pierens, Tina S. Skinner‐Adams, Katherine T. Andrews, Paul V. Bernhardt, Elizabeth H. Krenske, Ernesto Mollo, Mary J. Garson,

Synthesis and Catalytic Reactions

Five new isocyano/isothiocyanato sesquiterpenes (1–5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26–0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.