Enantioselective total synthesis of FD-891

Journal of the American Chemical Society
Michael T Crimmins, Franck Caussanel

Abstract

The enantioselective synthesis of FD-891 has been achieved with a longest linear sequence of 21 steps. The synthetic strategy involves the use of aldol additions of a chlorotitanium enolate of N-acylthiazolidinethiones as the key reaction to establish 6 of the 10 stereogenic centers. A key cross-metathesis and a late-stage Julia olefination serve to assemble three key subunits.

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Citations

Sep 26, 2012·Chemical Reviews·A ParentyJ-M Campagne
Nov 13, 2012·The Journal of Organic Chemistry·J S YadavG Sabitha
Jun 16, 2006·Organic Letters·Jorge García-FortanetJ Alberto Marco
May 5, 2006·Organic Letters·Michael T Crimmins, David J Slade
Mar 4, 2008·Chemical & Pharmaceutical Bulletin·Takahiro MiyakeHiroyuki Akita
May 28, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xufen Yu, Dianqing Sun
Nov 17, 2006·Angewandte Chemie·Dustin J CovellM Christina White
May 23, 2007·Chemistry : a European Journal·Jorge García-FortanetIsabel Barasoain
Dec 3, 2015·Chembiochem : a European Journal of Chemical Biology·Tadashi EguchiAkimasa Miyanaga
Aug 22, 2012·Chemistry, an Asian Journal·Qiang ChenXuegong She
Aug 5, 2008·The Journal of Organic Chemistry·Gerald Enderlin, Poul Nielsen
Dec 12, 2007·Organic Letters·Jorge EstebanJaume Vilarrasa
Sep 26, 2019·Organic Letters·Satyanarayana Nyalata, Sadagopan Raghavan

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