Further Synthesis of Optically Active Verrucarinic Acid

Article abstract of DOI:10.1002/hlca.19840670631

Two new syntheses of verrucarinic acid ((2S,3R)-2,5-dihydroxy-3-methylpentanoic acid) and its derivatives, suitably protected for the further conversion to macrocyclic trichothecenes, are described.The first one makes use of a diastereoselective alkylation of a (-)-(S)-malic acid ester and the regioselective reduction of one carboxyl function to a methyl group.The second approach involves a stereoselective addition of an allylsilane to a chiral glyoxylate.