A New Concise Synthesis of Methylenomycin B
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (08) , 575-576
- https://doi.org/10.1055/s-1991-20803
Abstract
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.Keywords
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