Total Syntheses of HMP-Y1, Hibarimicinone, and HMP-P1

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Total Syntheses of HMP-Y1, Hibarimicinone, and HMP-P1

Show simple item record Liau, Brian Bor-Jen Milgram, Benjamin Charles Shair, Matthew David 2012-09-26T12:34:17Z 2012
dc.identifier.citation Liau, Brian B., Benjamin C. Milgram, Matthew D. Shair. 2012. Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1. Journal of the American Chemical Society 134(40): 16765–16772. en_US
dc.identifier.issn 0002-7863 en_US
dc.identifier.issn 1520-5126 en_US
dc.description.abstract Total syntheses of HMP-Y1, atrop-HMP-Y1, hibarimicinone, atrop-hibarimicinone, and HMP-P1 are described using a two-directional synthesis strategy. A novel benzyl fluoride Michael–Claisen reaction sequence was developed to construct the complete carbon skeleton of HMP-Y1 and atrop-HMP-Y1 via a symmetrical, two-directional, double annulation. Through efforts to convert HMP-Y1 derivatives to hibarimicinone and HMP-P1, a biomimetic mono-oxidation to desymmetrize protected HMP-Y1 was realized. A two-directional unsymmetrical double annulation and biomimetic etherification were developed to construct the polycyclic and highly-oxidized skeleton of hibarimicinone, atrop-hibarimicinone, and HMP-P1. The use of a racemic biaryl precursor allowed for the synthesis of both hibarimicinone atropisomers and provides the first confirmation of the structure of atrop-hibarimicinone. Additionally, this work documents the first reported full characterization of atrop-hibarimicinone, HMP-Y1, atrop-HMP-Y1, and HMP-P1. Lastly, a pH-dependent rotational barrier about the C2–C2' bond of hibarimicinone was discovered, which provides valuable information necessary to achieve syntheses of the glycosylated congeners of hibarimicinone. en_US
dc.description.sponsorship Chemistry and Chemical Biology en_US
dc.language.iso en_US en_US
dc.publisher American Chemical Society en_US
dc.relation.isversionof doi:10.1021/ja307207q en_US
dash.license OAP
dc.title Total Syntheses of HMP-Y1, Hibarimicinone, and HMP-P1 en_US
dc.type Journal Article en_US
dc.description.version Accepted Manuscript en_US
dc.relation.journal Journal of the American Chemical Society en_US Shair, Matthew David 2012-09-26T12:34:17Z

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