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

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Published

2013-06-13

Issue

No. 5 (2013)

Section

Original Papers