Please use this identifier to cite or link to this item: https://doi.org/10.1021/ol102390t
Title: A bismuth(III)-catalyzed friedel-crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin
Authors: Eey, S.T.-C.
Lear, M.J. 
Issue Date: 3-Dec-2010
Source: Eey, S.T.-C., Lear, M.J. (2010-12-03). A bismuth(III)-catalyzed friedel-crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin. Organic Letters 12 (23) : 5510-5513. ScholarBank@NUS Repository. https://doi.org/10.1021/ol102390t
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 LiClO4 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. © 2010 American Chemical Society.
Source Title: Organic Letters
URI: http://scholarbank.nus.edu.sg/handle/10635/92924
ISSN: 15237060
DOI: 10.1021/ol102390t
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