期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 2, 页码 405-409出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303328
关键词
centrolobine; decytospolides; stereoselectivity; tetrahydropyrans; total synthesis
资金
- Nanyang Technological University [RG50/08]
- NMRC from the Ministry of Health, Singapore [H1N1 R/001/2009]
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 regioand 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 b-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.
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