Stereochemistry of Deconjugative Alkylation of Ester Dienolates. Stereospecific Total Synthesis of the Litsenolides

Article abstract of DOI:10.1021/jo00340a041

Deconjugative protonations, alkylations, and aldol condensations of the dienolates from (Z)-2-alkenoates give the corresponding (E)-3-enoate products, whereas dienolates from (E)-2-enoates give mainly the (Z)-3-enoate products.These generalizations are exploited in stereospecific total syntheses of litsenolides A₂, B₂, and C₂.