@article {107791,
	title = {Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1.},
	journal = {J Am Chem Soc},
	volume = {134},
	year = {2012},
	month = {2012 Oct 10},
	pages = {16765-72},
	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 was 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. Last, a pH-dependent rotational barrier about the C2-C2{\textquoteright} bond of hibarimicinone was discovered, which provides valuable information necessary to achieve syntheses of the glycosylated congeners of hibarimicinone.},
	keywords = {Actinobacteria, Antineoplastic Agents, Biomimetics, Ethers, Glycosides, Naphthacenes, Oxidation-Reduction, Stereoisomerism},
	issn = {1520-5126},
	doi = {10.1021/ja307207q},
	author = {Liau, Brian B. and Milgram, Benjamin C. and Shair, Matthew D.}
}
