A NEW CONCISE SYNTHESIS OF METHYLENOMYCIN-B

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-pentenyl-phosphonate...

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Bibliographic Details
Published inSynlett no. 8; pp. 575 - 576
Main Authors MIKOLAJCZYK, M, ZURAWINSKI, R
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.1991
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BETA-KETOPHOSPHONATE
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Summary: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-pentenyl-phosphonate (5) and the Horner-Emmons reaction of diethyl 3,4-dimethyl-2-oxo-3-cyclopentenylphosphonate (6) with formaldehyde.
ISSN:0936-5214
DOI:10.1055/s-1991-20803