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

DSpace/Manakin Repository

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

Show simple item record

dc.contributor.author Liau, Brian Bor-Jen
dc.contributor.author Milgram, Benjamin Charles
dc.contributor.author Shair, Matthew David
dc.date.accessioned 2012-09-26T12:34:17Z
dc.date.issued 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.identifier.uri http://nrs.harvard.edu/urn-3:HUL.InstRepos:9639969
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
dash.depositing.author Shair, Matthew David
dc.date.available 2012-09-26T12:34:17Z

Files in this item

Files Size Format View
JACS_Shair to be deposited to DASH.pdf 1.314Mb PDF View/Open

This item appears in the following Collection(s)

  • FAS Scholarly Articles [7362]
    Peer reviewed scholarly articles from the Faculty of Arts and Sciences of Harvard University

Show simple item record

 
 

Search DASH


Advanced Search
 
 

Submitters