Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin

Journal of the American Chemical Society
Mark S TichenorDale L Boger

Abstract

The total synthesis of the reported structure 2 for yatakemycin, an exceptionally potent, naturally occurring antitumor agent disclosed in 2003, and its lack of correlation with the natural product are detailed. On the basis of spectroscopic distinctions between 2 and yatakemycin, the natural product structure was reformulated as 3, now bearing a thiomethyl ester versus thioacetate in the left-hand subunit. Total synthesis of 3 provided a compound nearly identical to but still subtly distinct from the natural product. A second reformulation of the yatakemycin structure as 1, incorporating the alternatively substituted right-hand subunit as well as the initial thiomethyl ester reformulation, was confirmed by total synthesis of both (+)- and ent-(-)-1 in studies that also unambiguously established the absolute configuration of the natural product.

References

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Citations

Aug 19, 2007·Journal of the American Chemical Society·Mark S TichenorDale L Boger
Nov 21, 2007·Journal of the American Chemical Society·Wei JinDale L Boger
Jun 26, 2009·Journal of the American Chemical Society·Karen S MacMillan, Dale L Boger
Jan 22, 2009·Journal of the American Chemical Society·Karen S MacMillanDale L Boger
Jun 2, 2012·Journal of Medicinal Chemistry·Amanda L WolfeDale L Boger
May 1, 2013·Journal of Medicinal Chemistry·Amanda L WolfeDale L Boger
Jul 31, 2009·Journal of Medicinal Chemistry·Karen S MacMillan, Dale L Boger
Jan 22, 2011·The Journal of Organic Chemistry·David W LinPhil S Baran
Jan 18, 2006·Nature Chemical Biology·John D TrzupekDale L Boger
Nov 29, 2005·Natural Product Reports·Tomomi Kawasaki, Kazuhiro Higuchi
May 13, 2010·Chemical Communications : Chem Comm·Kentaro OkanoHidetoshi Tokuyama
Sep 12, 2015·The Journal of Organic Chemistry·Michael J StephensonMark Searcey
Jun 14, 2013·Cancer Biology & Therapy·George A VielhauerDale Boger
Dec 22, 2004·Chemistry & Biology·Winston C Tse, Dale L Boger
Oct 23, 2004·Bioorganic & Medicinal Chemistry·Jay P ParrishDale L Boger
Jul 7, 2018·Angewandte Chemie·Zheng HuangJean-Philip Lumb
Nov 16, 2007·Chemistry, an Asian Journal·Kentaro OkanoTohru Fukuyama
Oct 12, 2010·Natural Product Reports·Ian S YoungAlison Thompson
Apr 16, 2019·Critical Reviews in Microbiology·Ellis C O'NeillNatalie Millán-Aguiñaga
Aug 28, 2015·Archives of Pharmacal Research·Hye-Dong YooMin-Sun Kim
Apr 5, 2008·Natural Product Reports·Mark S Tichenor, Dale L Boger
Dec 6, 2014·The Journal of Biological Chemistry·Matthew R BauerleSquire J Booker
Mar 18, 2011·Natural Product Reports·Scott A SnyderFerenc Kontes
Oct 12, 2010·Chemistry : a European Journal·Jason C Kwan, Hendrik Luesch
Mar 20, 2018·Bioorganic & Medicinal Chemistry Letters·Konstantinos KiakosPravin C Patil
Jan 5, 2011·The Journal of Organic Chemistry·James P Lajiness, Dale L Boger
Aug 27, 2005·The Journal of Organic Chemistry·Mauro Freccero, Remo Gandolfi

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