A bismuth(III)-catalyzed Friedel-Crafts cyclization and stereocontrolled organocatalytic approach to
Stanley T-C Eey1, Martin J Lear
1Department of Chemistry, Faculty of Science, and Medicinal Chemistry Program of the Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
Abstract:
A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO(4) to suppress the Lewis basicity of the sulfonate group. After TBAF-promoted cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.
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