The Isolation and Synthesis of Novel Nematocidal Dithiocyanates from an Australian Marine Sponge, Oceanapia sp.

Robert J. Capon, Colin Skene, Edward Hsiang-Te Liu, Ernest Lacey, Jennifer H. Gill, Kirstin Heiland, and Thomas Friedel

Journal of Organic Chemistry, 2001, 66, 7765-7769.

Publication Date: October 2, 2001


Bioassay-directed fractionation of the EtOH extract of an Oceanapia sp. collected off the northern Rottnest Shelf, Australia, has yielded three novel dithiocyanates, thiocyanatins A (1), B (2a), and C (2b). The structures were determined by detailed spectroscopic analysis and confirmed by total synthesis. In addition to featuring an unprecedented dithiocyanate functionality, thiocyanatins possess an unusual 1,16-difunctionalized n-hexadecane carbon skeleton and are revealed as a hitherto unknown class of nematocidal agent.

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