Facile access to cis-2,6-disubstituted tetrahydropyrans by palladium-catalyzed decarboxylative allylation : total syntheses of (±)-centrolobine and (+)-decytospolides A and B
Tan, Yu Jia
Leow, Min Li
Date of Issue2014
School of Physical and Mathematical Sciences
cis-2,6-Tetrahydropyran is an important structural skeleton of bioactive natural products. A facile synthesis of cis-2,6-disubstituted-3,6-dihydropyrans as cis-2,6-tetrahydropyran precursors has been achieved in high regio- and stereoselectivity with high yields. This reaction involves a palladium-catalyzed decarboxylative allylation of various 3,4-dihydro-2H-pyran substrates. Extending this reaction to 1,2-unsaturated carbohydrates allowed the achievement of challenging β-C-glycosylation. Based on this methodology, the total syntheses of (±)-centrolobine and (+)-decytospolides A and B were achieved in concise steps and overall high yields.
DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
Chemistry - a European journal
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.