American Chemical Society
ol203466m_si_005.cif (15.82 kB)

Practical Syntheses of Proposed and Revised Manzacidin B and Their Congeners

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posted on 2012-02-17, 00:00 authored by Kuppusamy Sankar, Hasibur Rahman, Pragna P. Das, Eswar Bhimireddy, B. Sridhar, Debendra K. Mohapatra
A concise and highly stereoselective total synthesis of manzacidin B and its congeners has been developed following chelation-controlled syn-epoxidation and Lewis acid catalyzed intramolecular regioselective epoxide ring opening to generate the quarternary amine center. Elaboration of the triol moiety to the target molecule was achieved in good overall yield, representing practical total syntheses of manzacidin B and its congeners. From the XRD, NMR, and analytical data, the correct structure of natural manzacidin B, (4R,5R,6R)-6, was confirmed.