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Synlett 1991; 1991(8): 575-576
DOI: 10.1055/s-1991-20803
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A New Concise Synthesis of Methylenomycin B

Marian Mikołajczyk* , Remigiusz Zurawiński
  • *Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, PL-90-363 Lódz, Sienkiewicza 112, Poland
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Publikationsdatum:
07. März 2002 (online)

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Methylenomycin B (1; 2,3-dimethyl-5-methylene-2-cyclopenten-1-one) has been synthesized from diethyl methylphosphonate (2) in four steps in overall 24% yield. The key steps in this synthesis involve the intramolecular carbenoid cyclization of diethyl 1-diazo-3,4-dimethyl-2-oxo-3-pentenylphosphonate (5) and the Horner-Emmons reaction of diethyl 3,4-dimethyl-2-oxo-3-cyclopentenylphosphonate (6) with formaldehyde.

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