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Synfacts 2011(3): 0241-0241  
DOI: 10.1055/s-0030-1259412
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of the Proposed Structure of Briarellin J

Contributor(s): Steven V. Ley, Sean Newton
M. T. Crimmins*, M. C. Mans, A. D. Rodríguez
University of North Carolina at Chapel Hill, USA and University of Puerto Rico, San Juan, Puerto Rico
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

The briarellins A-P were isolated from alcyonarians (octocoral) located in the Caribbean and Pacific Ocean. The relative stereochemistry was proposed from NMR spectroscopy and comparative NOESY studies. The absolute configurations of briarellins E and F have been confirmed by total synthesis. The above synthesis did not correspond to the isolated natural product. A ­revised structure is proposed based on further NOESY studies and crystallographic data of an advanced intermediate.