Total synthesis of (-)-minquartynoic acid: An anti-cancer, anti-HIV natural product

[GRAPHIC] The tetraacetylenic compound, (S)-minquartynoic acid (1), is synthesized in seven linear steps and 17% overall yield from commercially available azelaic acid monomethyl ester. The key step is a one-pot three-component Cadiot-Chodkiewiez reaction to construct the tetrayne unit without using either a diyne or a triyne intermediate.