Journal
ORGANIC LETTERS
Volume 12, Issue 23, Pages 5510-5513Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102390t
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- National University Singapore
- National Research Foundation [NRF-G-CRP 2007-04]
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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 LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl 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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