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Strategies for the stereocontrolled preparations of 2,6- cis - and 2,6- trans -substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in S E ′ reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at −78...
The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly...
While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new...
A highly diastereoselective iron-catalyzed synthesis of substituted cis -2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives is described. The FeCl 3 ·6H 2 O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high...
A diastereoselective synthesis of 2,6- cis -tetrahydropyranyl acetic acids has been developed based on the palladium(II)-catalysed intramolecular hydroxycarbonylation of hexenols. This domino Pd-cyclisation/carbonylation/hydroxylation of (2 S )-hept-6-en-2-ol 15 and O -TBDPS protected...
The corresponding oxadiene, prepared from the starting perbenzylated α- d -mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3- C -α- d -mannosylated 1,2- d...
The combination of an ‘ene’ reaction between a 2-(2-trialkylsilyloxyalkyl)prop-2-enyl(trimethyl)silane and an alk-1-yn-3-one mediated by zinc(II) iodide, and an intramolecular oxy-Michael reaction, provides an efficient synthesis of cis -2,6-disubstituted 4-methylenetetrahydropyrans of...
In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an...
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