Total synthesis of (-)-minquartynoic acid: an anti-cancer, anti-HIV natural product.
[structure: see text] 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-Chodkiewicz reaction to construct the tetrayne unit without using either a diyne or a triyne intermediate.
Gung
Benjamin W
BW
Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, USA. gungbw@muohio.edu
Dickson
Hamilton
H
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000871:Anthelmintics / Q000138:chemical synthesis; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003998:Dicarboxylic Acids / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D006801:Humans; D010946:Plants, Medicinal / Q000737:chemistry; D053279:Polyynes; D013237:Stereoisomerism
D000480:Alkynes; D000871:Anthelmintics; D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D003998:Dicarboxylic Acids; D005231:Fatty Acids, Unsaturated; C417933:minquartynoic acid; D053279:Polyynes; C010038:azelaic acid