(+)-Zwittermicin A. Rapid Assembly of C9-C15 and a Formal Total Synthesis

Department of Chemistry and Biochemistry and Skaggs School of Pharmacy, University of California, San Diego, 9500 Gilman Dr., La Jolla, California 92093, USA.
The Journal of Organic Chemistry (Impact Factor: 4.72). 09/2009; 74(20):7660-4. DOI: 10.1021/jo901007v
Source: PubMed


A short, enantioselective synthesis of the C9-C15 portion of (+)-zwittermicin A is reported that exploits directional functionalization of the known hepta-2,5-diyne-1,7-diol by partial reduction of the two triple bonds followed by Sharpless asymmetric epoxidation and boron-directed double ring-opening with sodium azide under Miyashita conditions. Subsequent desymmetrization of the C(2)-symmetric diazidotetraol product converges upon (-)-3--the enantiomer of the key intermediate of our earlier structural proof and synthesis of (-)-zwittermicin A--and constitutes a formal synthesis of (+)-zwitttermicin A.

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Available from: Tadeusz F Molinski, Jun 26, 2014
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