@article { ISI:000269257800009,
	title = {Synthesis and conformational study of chiral oxepines: the baylis-hillman reaction and RCM approach with sugar aldehyde},
	journal = {Journal of Organic Chemistry},
	volume = {74},
	number = {17},
	year = {2009},
	month = {SEP},
	pages = {6486-6494},
	publisher = {AMER CHEMICAL SOC},
	address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA},
	abstract = {<p>The Baylis-Hillman reaction of 3-O-allyl-alpha-D-xylo-pentodialdo-1,4-furanose 3 afforded a diastereomeric mixture of D-gluco- and L-ido-configured alpha-methylene-beta-hydroxy esters 4a and 4b, respectively, in a ratio of 2:3. Reduction of the ester functionality in 4a/4b gave alcohols 5a/5b. The diene thus formed in 5a/5b was subjected to ring-closing metathesis (Grubbs{\textquoteright} second-generation catalyst) to afford oxa-bicyclic ring system 6a/6b in high yield. Further manipulation of the aectonide functionality in 6a and 6b afforded new polyhydroxylated oxepines 1a/2a and 1b/2b, respectively. The (1)H NMR of oxepines 1a and 1b in D(2)O showed doubling of signals indicating their existence in two different rotamers/conformers. This fact was substantiated by calculating energetics of 1 and 2 conformers using the density functional theory and correlating the calculated (1)H NMR chemical shift pattern with that of the experimental spectra.</p>},
	issn = {0022-3263},
	doi = {10.1021/jo900660q},
	author = {Jadhav, Vrushali H. and Bande, Omprakash P. and Pinjari, Rahul V. and Gejji, Shridhar P. and Puranik, Vedavati G. and Dhavale, Dilip D.}
}
