Stereoselective alkylation of tartrate derivatives. A concise route to (+)-O-methylpiscidic acid and natural analogues.
The lithium enolate of (2S,3S,5S,6S)-dimethoxy-2,3-dimethyl-1,4-dioxane-5,6-dithiocarboxylate undergoes stereoselective mono- and/or dialkylations to afford two new stereogenic centers. The alkylation products obtained possessed a cis stereochemistry, which was confirmed by the synthesis of natural 4'-O-methylpiscidic acid dimethyl ester .
Burke
Anthony J
AJ
Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Oeiras, Portugal.
Maycock
Christopher D
CD
Ventura
M Rita
MR
D000478:Alkylation; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
D062385:Hydroxybenzoates; D010936:Plant Extracts; D013644:Tartrates; C030971:piscidic acid