A Concise Synthesis of (-)-Methylenolactocin and (-)-Phaseolinic Acid from (6S,9S)-Tetradec-7-yne-6,9-diol
31 December 2001 (online)
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