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

Авторы

  • 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

Ключевые слова:

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

Аннотация

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

Биографии авторов

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

Загрузки

Опубликован

2013-06-13

Выпуск

№ 5 (2013)

Раздел

Оригинальные статьи