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Synthesis 2001; 2001(3): 0403-0408
DOI: 10.1055/s-2001-11432
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A Convenient Synthesis of 3-Alkylidenetetrahydro-2-furanones from 3-Diethoxyphosphoryl-2,5-dihydro-2-furanones

Tomasz Janecki* , Edyta Błaszczyk
  • *Institute of Organic Chemistry, Technical University, Żeromskiego 116, 90-924 Łódź, Poland; Fax + (42)6 36 55 30; E-mail: tjanecki@ck-sg.p.lodz.pl
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Publication Date:
31 December 2001 (online)

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A versatile route to 3-alkylidenetetrahydro-2-furanones, 10, 13, 14, and 15 was developed by employing a two step reaction sequence consisting of Michael addition of various nucleophiles to 3-diethoxyphosphoryl-2,5-dihydro-2-furanone 4 and subsequent olefination of formaldehyde and other aldehydes with adducts 6 a - g. This method was also applied to the synthesis of furochromenone 18 and furopyrrolizinone 19.

Michael additions - Horner-Wadsworth-Emmons alkenations - phosphorylated lactones - 2,5-dihydro-2-furanones - 3-alkylidenetetrahydro-2-furanones