Issue 16, 2011
From the journal:

Organic & Biomolecular Chemistry

Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2-substituted furans: Application to the biomimetic synthesis of merrekentrone C†

Charis Gryparis,a   Ioannis N. Lykakis,‡a   Christina Efe,a   Ioannis-Panayotis Zaravinos,a   Theonymphi Vidali,a   Eugenia Kladoua  and  Manolis Stratakis*a  

* Corresponding authors

a Department of Chemistry, University of Crete, Voutes, Iraklion, Greece
E-mail: stratakis@chemistry.uoc.gr
Fax: +30 2810 545001
Tel: +30 2810 545087

Abstract

Photooxygenation of (β-keto)-2-substituted furans leads, in a one pot operation, to functionalized 3(2H)-furanones with good to excellent yields. This methodology was applied as a key-step to the concise and biomimetic synthesis of the sesquiterpene merrekentrone C. The precursor to merrekentrone C, keto difuran, was synthesized using a cross coupling of α-iodo-3-acetylfuran with an alkenyl furan under Fenton-type conditions.

Graphical abstract: Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2-substituted furans: Application to the biomimetic synthesis of merrekentrone C

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Article information

DOI
https://doi.org/10.1039/C1OB05567D
Article type
Communication
Submitted
09 Apr 2011
Accepted
14 Jun 2011
First published
27 Jun 2011

Org. Biomol. Chem., 2011,9, 5655-5658

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Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2-substituted furans: Application to the biomimetic synthesis of merrekentrone C

C. Gryparis, I. N. Lykakis, C. Efe, I. Zaravinos, T. Vidali, E. Kladou and M. Stratakis, Org. Biomol. Chem., 2011, 9, 5655 DOI: 10.1039/C1OB05567D

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