Stereoselective total synthesis of (+)-pinellic acid from l-(+)-tartaric acid

The stereoselective total synthesis of (+)-pinellic acid, a natural product used in the treatment of influenza, was accomplished from l-(+)-tartaric acid. A key feature of the synthesis includes the elaboration of a γ-hydroxybutyramide derived from l-(+)-tartaric acid.

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(4R,5R)-5-Hexanoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamideC14H25NO4[α]D25=+15.4 (c 2.2, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4R,5R)

(R)-Methyl 2-hydroxy-2-((4R,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)acetateC13H24O5[α]D25=+21.3 (c 0.5, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4R,5R)

(E)-Methyl 11-((4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)-9-oxoundec-10-enoateC22H38O5[α]D25=+6.3 (c 0.6, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (E,4S,5R)

(E,9R,12R,13R)-Methyl 9,12,13-trihydroxyoctadec-10-enoateC19H36O5[α]D25=+10 (c 0.8, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (E,9R,12R,13R)

(E,9R,12R,13R)-9,12,13-Trihydroxyoctadec-10-enoic acidC18H34O5[α]D25=+12 (c 1, MeOH)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (E,9R,12R,13R)