Eey, Stanley T.-C. and Lear, Martin J. (2010) A bismuth(III)-catalyzed Friedel−Crafts cyclization and stereocontrolled organocatalytic approach to (−)-platensimycin. Organic Letters, 12 (23). pp. 5510-5513. ISSN 1523-7060
Full content URL: http://dx.doi.org/10.1021/ol102390t
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| Item Type: | Article |
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| Item Status: | Live Archive |
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.
| Keywords: | Total synthesis, Natural product, Bismuth, Conjugate reduction, Stereoselective |
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| Subjects: | F Physical Sciences > F160 Organic Chemistry |
| Divisions: | College of Science > School of Chemistry |
| ID Code: | 17108 |
| Deposited On: | 16 Apr 2015 14:09 |
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