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Title: | Facile access to cis-2,6-disubstituted tetrahydropyrans by palladium-catalyzed decarboxylative allylation : total syntheses of (±)-centrolobine and (+)-decytospolides A and B | Authors: | Zeng, Jing Tan, Yu Jia Ma, Jimei Leow, Min Li Tirtorahardjo, Davin Liu, Xue-Wei |
Keywords: | DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds | Issue Date: | 2014 | Source: | Zeng, J., Tan, Y. J., Ma, J., Leow, M. L., Tirtorahardjo, D., & Liu, X.-W. (2014). Facile access to cis-2,6-disubstituted tetrahydropyrans by palladium-catalyzed decarboxylative allylation : total syntheses of (±)-centrolobine and (+)-decytospolides A and B. Chemistry - A European Journal, 20(2), 405-409. | Series/Report no.: | Chemistry - a European journal | Abstract: | 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. | URI: | https://hdl.handle.net/10356/100876 http://hdl.handle.net/10220/18986 |
ISSN: | 0947-6539 | DOI: | 10.1002/chem.201303328 | Schools: | School of Physical and Mathematical Sciences | Rights: | © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Fulltext Permission: | none | Fulltext Availability: | No Fulltext |
Appears in Collections: | SPMS Journal Articles |
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