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The remarkable effect of cosolvent on a samarium(II)-mediated 4-exo-trig cyclization: Further synthetic studies on pestalotiopsin A

Author(s): D. J. Edmonds, K. W. Muir, D. J. Procter

A samarium(II)-mediated 4-exo-trig cyclization in which a remote stereocenter serves to control the facial selectivity of the cyclization is described. The apparent coordination of a tert-butyldimethylsilyl ether to the samarium center appears to give rise to the selectivity. The remarkable effect of the cosolvent, 2,2,2-trifluoroethanol, on the cyclization of this substrate, is also discussed. A stereoselective synthesis of the general class of gamma,delta-unsaturated aldehyde cyclization substrate is reported, and the utility of the cyclization is demonstrated in an approach to the fully functionalized core of pestalotiopsin A.

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ISBN: 0022-3263
Publication Year: 2003
Periodical: Journal of Organic Chemistry
Periodical Number: 8
Volume: 68
Pages: 3190-3198
Author Address: