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Synthesis of Tetrahydropyran/Tetrahydrofuran‐Containing Macrolides by Palladium‐Catalyzed Alkoxycarbonylative Macrolactonizations
Author(s) -
Bai Yu,
Davis Dexter C.,
Dai Mingji
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403006
Subject(s) - tetrahydropyran , tetrahydrofuran , palladium , chemistry , catalysis , combinatorial chemistry , ring (chemistry) , stereochemistry , cascade , organic chemistry , solvent , chromatography
A novel Pd‐catalyzed cascade alkoxycarbonylative macrolactonization to construct tetrahydropyran/tetrahydrofuran‐containing bridged macrolactones in one step from alkendiols is described. Products with various ring sizes and substituents were obtained. Challenging macrolactones involving tertiary alcohols were synthesized smoothly as well. Mechanistically, experimental evidence to support a trans‐oxypalladation step has been provided. The method was applied to the synthesis of potent anticancer compound 9‐demethylneopeltolide.