Facile Access to cis-2,6-Disubstituted Tetrahydropyrans by Palladium-Catalyzed Decarboxylative Allylation: Total Syntheses of (±)-Centrolobine and (+)-Decytospolides A and B.

Autor: Zeng, Jing, Tan, Yu Jia, Ma, Jimei, Leow, Min Li, Tirtorahardjo, Davin, Liu, Xue‐Wei
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Zdroj: Chemistry - A European Journal; Jan2014, Vol. 20 Issue 2, p405-409, 5p
Abstrakt: 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-2 H-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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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