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Synfacts 2013; 9(1): 0016
DOI: 10.1055/s-0032-1317851
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Formal Syntheses of (±)-Laurefucin and (±)-E- and (±)-Z-Pinnatifidenyne

Contributor(s):
Erick M. Carreira
,
Julian Egger
Snyder SA, * Brucks AP, Treitler DS, Moga I. Columbia University, New York, USA
Concise Synthetic Approaches for the Laurencia Family: Formal Total Syntheses of (±)-Laurefucin and (±)-E- and (±)-Z-Pinnatifidenyne.

J. Am. Chem. Soc. 2012;
134: 17714-17721
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

bromoetherification - ring expansion - lauroxocanes - haloethers

Significance

(±)-Laurefucin and (±)-E- and (±)-Z-pinnatifidenyne are oxocanes belonging to the class of Laurencia haloethers. The authors implement a previously developed bromoetherification–ring-expansion sequence to obtain the stereochemically rich medium-sized rings present in the natural products.


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Comment

Treatment of highly functionalized tetrahydrofuran substrates D and O with bromonium source E, induces a haloetherification giving oxonium intermediates F and P. Subsequent intramolecular trapping by an internal nucleophile provides previously reported cyclic ethers G and R.


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