Synthesis of Plakortone B

M. F. Semmelhack; R. J. Hooley; C. M. Kraml

doi:10.1055/s-2007-968291

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Synfacts 2007(4): 0348-0348
DOI: 10.1055/s-2007-968291

Synthesis of Natural Products and Potential Drugs

Synthesis of Plakortone B

Contributor(s): Philip Kocienski, Zofia Komsta
M. F. Semmelhack*, R. J. Hooley, C. M. Kraml
Princeton University and Wyeth Research, Princeton, USA

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Publication History

Publication Date:
23 March 2007 (online)

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Significance

The plakortones, isolated from Plakortis halichondrioides and Plakortis simplex, stimulate the cardiac sacroplasmic reticulum Ca²⁺ ATPase. The focal points of this synthesis are (1) coupling of boron-ate H and vinyl iodide F by a modified Suzuki reaction, and (2) formation of the furanolactone core by intramolecular alkoxypalladation-lactonization.