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

Charis Gryparis; Ioannis N. Lykakis; Christina Efe; Ioannis-Panayotis Zaravinos; Theonymphi Vidali; Eugenia Kladou; Manolis Stratakis

doi:10.1039/C1OB05567D

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 Kladou^a and Manolis Stratakis*^a

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* Corresponding authors

^a Department of Chemistry, University of Crete, Voutes, 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.

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Publication details

The article was received on 09 Apr 2011, accepted on 14 Jun 2011 and first published on 27 Jun 2011

Article type: Communication

DOI: 10.1039/C1OB05567D

Citation: 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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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Publication details

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

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