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Synthesis 1999; 1999(2): 282-285
DOI: 10.1055/s-1999-3390
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First One-Pot Synthesis of Mikanecic Acid Derivatives from Allylic Phosphonates, via a Tandem-Sequence Horner-Wadworth-Emmons and Diels-Alder Reactions

Hashim Al-Badri* , Noël Collignon
  • *Laboratoire d'Hétérochimie Organique de l'IRCOF, Université de Rouen-INSAR, Place E. Blondel, BP 08, F-76131 Mont-Saint-Aignan Cedex, France; Fax +(33)02 35 52 29 59; E-mail: Noël.Collignon@insa-rouen.fr
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Publication History

Publication Date:
31 December 1999 (online)

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This paper describes a new, simple, general and efficient one-pot synthesis of mikanecic acid derivatives from allylic phosphonates, ethyl chloroformate and aqueous formaldehyde. The overall process involves a cascade sequence linking together metallation-alkoxycarbonylation, Horner-Wadworth-Emmons and Diels-Alder reactions.

allylphosphonates - α-ethoxycarbonylallylphosphonates - mikanecic acid derivatives - alkenation - cycloaddition - one-pot synthesis

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