Total Syntheses of (-)-18-Hydroxyminquartynoic Acid, (S)-E-15,16-Dihydrominquartynoic Acid, and Analogs of Minquartynoic Acid, and Antibacterial Properties of Some Selected Polyacetylenic Compounds

by Kumi, Godwin K

(S)-Minquartynoic acid, (S)-18-Hydroxyminquartynoic acid, and (E)-15,16-Dihydromin-quartynoic acid are polyacetylenic natural products. In recent in vitro tests, all three polyacetylenes show potent cytotoxicity, against 10 different tumor cell lines. We accomplishedthe total synthesis of (S)-18-Hydroxyminquartynoic acid, by a triple convergent synthesis. The key step in making (E)-15,16-Dihydrominquartynoic acid is a one-pot desilylation Cadoit-Chodkiewicz cross-coupling reaction to construct the entriyne unit. The anti-bacterial activities of these three natural products were tested. We designed andsynthesized analogs of minquartynoic acid, because of its remarkable activity against Staphylococcus aureus. Some of the analogs has the highest potency against Staphylococcusaureus and Streptococcus pyogenes.