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Syntheses of the Carotane-type Terpenoids (+)-Schisanwilsonene A and (+)-Tormesol via a Two-Stage Approach.
Org Lett
January 2021
State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Stereoselective syntheses of terpenoids in a more efficient manner have been a long-term pursuit for synthetic chemists. Herein we describe the two-step, enantiospecific and protecting-group-free synthesis of (+)-schisanwilsonene A from a carotane compound, which was produced in . We also completed the first enantiomeric synthesis of (+)-tormesol in five steps.
View Article and Find Full Text PDFα,β-Unsaturated Gold(I) Carbenes by Tandem Cyclization and 1,5-Alkoxy Migration of 1,6-Enynes: Mechanisms and Applications.
Chemistry
September 2016
Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institut of Science and Technology (BIST), Av. Països Catalans 16, 43007, Tarragona, Spain.
1,6-Enynes bearing OR groups at the propargyl position generate α,β-unsaturated gold(I)-carbenes/ gold(I) stabilized allyl cations that can be trapped by alkenes to form cyclopropanes or 1,3-diketones to give products of α-alkylation. The best migrating group is p-nitrophenyl ether, which leads to the corresponding products without racemization. Thus, an improved formal synthesis of (+)-schisanwilsonene A has been accomplished.
View Article and Find Full Text PDFGold-catalyzed rearrangements and beyond.
Acc Chem Res
March 2014
Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain.
Cycloisomerizations of enynes are probably the most representative carbon-carbon bond forming reactions catalyzed by electrophilic metal complexes. These transformations are synthetically useful because chemists can use them to build complex architectures under mild conditions from readily assembled starting materials. However, these transformations can have complex mechanisms.
View Article and Find Full Text PDFSynthesis of (+)-schisanwilsonene A by tandem gold-catalyzed cyclization/1,5-migration/cyclopropanation.
Angew Chem Int Ed Engl
June 2013
Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain.
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