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Synlett 2001; 2001(1): 0120-0122
DOI: 10.1055/s-2001-9720
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A Concise Synthesis of (-)-Methylenolactocin and (-)-Phaseolinic Acid from (6S,9S)-Tetradec-7-yne-6,9-diol

Xavier Ariza* , Jordi Garcia, Marta López, Laia Montserrat
  • *Departament die Química Orgànica, Div. III, Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona, Catalonia, Spain; Fax +34 93 3 39 78 78; E-mail: jgarcia@qo.ub.es
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Publication Date:
31 December 2001 (online)

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A novel, stereodivergent route to paraconic acids from C 2-symmetric trans- and cis-alk-2-ene-1,4-diols through Ireland-Claisen and/or Johnson orthoester rearrangements is disclosed. This strategy has been applied to the synthesis of (-)-methylenolactocin and (-)-phaseolinic acid from a single chiral diol.

rearrangements - lactones - stereoselective synthesis - reductions