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Synthesis 1987; 1987(7): 659-661
DOI: 10.1055/s-1987-28041
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Methylenomycin B: A New Synthesis from a β-Ketophosphonate

Marian Mikołajczyk* , Piotr Bałczewski
  • *Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Organic Sulfur Compounds, Boczna 5, PL-90-362 Łódź, Poland
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Publication Date:
20 August 2002 (online)

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Methylenomycin B (1) was prepared from diethyl 2-oxopropanephosphonate (5) in four steps in 26% yield. The key steps in this synthesis include the Wittig-Horner reaction of 5 with methylthioethanal (7) followed by the 1,4-addition of a propionyl anion equivalent to the α-enone 4 formed affording 4-(methylthiomethyl)-hepta-2,5-dione (3) which is an acyclic precursor of the title antibiotic.

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