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

doi:10.1021/JO026827O

Paper

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

Published Mar 13, 2003 · David J. Edmonds, K. Muir, D. Procter

The Journal of organic chemistry

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50

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Abstract

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.

Study Snapshot

The samarium(II)-mediated 4-exo-trig cyclization allows for stereoselective synthesis of gamma,delta-unsaturated aldehyde substrates, potentially aiding in the fully functionalized core of pestalotiopsin A.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Citations

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