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[figure: see text] Carbohydrates as removable chiral scaffolds for free radical cyclizations were examined for the first time. This investigation illustrates the utility of two inexpensive carbohydrate derivatives as sources of asymmetry for 5-hexenyl radical cyclizations. Diastereomeric ratios as high as 100:1 were achieved with an ester-appended… (More)
[reaction: see text] A unique combination of highly enantio- and diastereoselective allylmetalations and a one-pot "desacetalization/spiroketalization" have been employed to synthesize the AB spiroketal fragment (C1-C13) of spongistatin in 15 steps and in excellent diastereoselectivity.
Experiments conducted with deuterated compounds demonstrated that during the reduction of S-alkylxanthates with triethylborane, the hydrogen atom transferred has several competing origins. Hydrogen abstraction from water (or an alcohol) is the most favourable route.