Chemoenzymatic synthesis of the C10-C23 segment of dictyostatin

Organic Letters
Evgeny PrusovMartin E Maier

Abstract

[reaction: see text] Employing enzymatic desymmetrization and resolution, respectively, the two aldehydes 8 and 20 were prepared. The precursor to aldehyde 8, meso-2,4-dimethylglutaric anhydride 3, could be obtained by base treatment of the diastereomeric mixture. Aldehyde 8 was extended to alkyne 10 by a Marshall reaction introducing four carbon atoms. Lithiation of the derived iodide 15 and trapping of the anion with amide 22 gave ketone 23. This compound led to the C10-C23 fragment 27 of dictyostatin.

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Citations

Jan 26, 2012·Organic Letters·Dawen Niu, Thomas R Hoye
Mar 27, 2013·Organic Letters·Sivappa RasapalliArnold L Rheingold
Oct 22, 2016·The Journal of Organic Chemistry·Vivek K MishraMartin E Maier
Mar 17, 2017·The Journal of Organic Chemistry·Luiz C Dias, Ellen C Polo
Jan 25, 2012·Angewandte Chemie·Shichao Yu, Shengming Ma
Dec 13, 2006·Angewandte Chemie·Matthew L MaddessSteven V Ley
May 15, 2013·Angewandte Chemie·Stephen HoJames L Leighton
Jan 26, 2008·Chemical Communications : Chem Comm·Chiara MontiCesare Gennari
Nov 18, 2010·Organic & Biomolecular Chemistry·Leticia Ferreiro-MederosFrançoise Colobert
Feb 11, 2009·Chemistry : a European Journal·Steven V LeyMichael C Willis
Jan 22, 2008·The Journal of Organic Chemistry·Richeng XuanHan-Young Kang
Jan 30, 2007·Organic Letters·Viktor V Vintonyak, Martin E Maier
Jun 5, 2007·Journal of Medicinal Chemistry·Won-Hyuk JungBilly W Day
Jan 11, 2007·Journal of the American Chemical Society·K C Nicolaou, Scott T Harrison
Aug 30, 2008·Tetrahedron·Youseung ShinDennis P Curran

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