FORMAL SYNTHESIS OF LAURENCIONE <i>via</i> MgBr2–CATALYZED REARRANGEMENT OF α,β-EPOXYKETONES TO 1,2-DIKETONES

Authors

  • D. Astashko Belorussian State University
  • Y. Habrus Belarusian State University
  • S. Yurevich Belarusian State University
  • V. Tyvorskii Belarusian State University

DOI:

https://doi.org/10.1007/355

Keywords:

cyclopropanols, α, β-epoxyketones, oxidation, 1, 2-diketones, 2­-hydroxytetrahydrofuran-3-ones

Abstract

A flexible method for synthesis of laurencione, a marine natural product, and its benzyl and tert-butyl-methylsilyl-protected precursors was developed utilizing 3-hydroxypropionic acid ethyl ester as a starting material. The synthetic route consists of Kulinkovich cyclopropanation of a hydroxyl-protected ester, followed by oxidation of the resulting cyclopropanol to the appropriate oxiranyl ketone and its MgBr2·OEt2-catalyzed rearrangement to 1,2‑diketone.

Also published in Chemistry of Heterocyclic Compounds, 2013, 49 (5), pp 676-682

http://link.springer.com/article/10.1007/s10593-013-1297-y

Author Biographies

D. Astashko, Belorussian State University

Dmitry Astashko

Y. Habrus, Belarusian State University

Yury Habrus

S. Yurevich, Belarusian State University

Sergei Yurevich

V. Tyvorskii, Belarusian State University

Vladimir Tyvorskii

Published

2013-06-13

Issue

Section

Original Papers