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
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.
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.
