Rhodium-Catalyzed Regio- and Enantioselective Addition of <i>N</i>-Hydroxyphthalimide to Allenes: A Strategy To Synthesize Chiral Allylic Alcohols
作者:Zi Liu、Bernhard Breit
DOI:10.1021/acs.orglett.7b03709
日期:2018.1.5
We achieved the first Rh-catalyzed regio- and enantioselectiveadditions of N-hydroxyphthalimide to allenes. This transformation is accomplished via mild reaction conditions, leveraging on Josiphos SL-J003-2 as a chiral ligand to furnish branched O-allyl compounds in good yields with moderate to excellent enantioselectivities. The substrate scope is broad, and various functional groups are tolerated
The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains. (C) 2008 Elsevier Inc. All rights reserved.