PREPARATIVE SCALE SYNTHESIS OF FUNCTIONALIZED BIOXAZOLE

Authors

  • Mihail Kazak Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga
  • Anna Vasilevska Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga
  • Edgars Suna Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga LV-1006, Latvia

DOI:

https://doi.org/10.1007/5535

Keywords:

bioxazole, diazonamide A, regioselective lithiation, transmetalation.

Abstract

Seven-step preparative scale synthesis of chiral, enantiomerically pure 2'-aminomethyl-2,4'-bioxazole has been accomplished from L-tert-Leu.
The 2,4'-bioxazole subunit can be functionalized at position C-5' by a regioselective lithiation, followed by the reaction with a suitable electrophile. The C-5'-lithium intermediate can be also transmetalated into organozinc species and used in Pd-catalyzed Negishi cross coupling.

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Published

2020-04-01

Issue

Vol. 56 No. 3 (2020)

Section

Original Papers