| 19746943 |
Rogers EW, Molinski TF: (+)-Zwittermicin A. J Org Chem. 2009 Oct 16;74(20):7660-4.
Rapid assembly of C9-C15 and a formal total synthesis. . 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. |
32(0,1,1,2) |