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

Abstract

[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.

• Authors: Benjamin W Gung, Hamilton Dickson
• Journal: Organic letters (Org Lett) Vol. 4 Issue 15 Pg. 2517-9 (Jul 25 2002) ISSN: 1523-7060 [Print] United States
• PMID: 12123365 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Alkynes
• Anthelmintics
• Anti-HIV Agents
• Antineoplastic Agents
• Dicarboxylic Acids
• Fatty Acids, Unsaturated
• minquartynoic acid
• Polyynes
• azelaic acid

Topics

• Alkynes (chemical synthesis, chemistry)
• Anthelmintics (chemical synthesis)
• Anti-HIV Agents (chemical synthesis)
• Antineoplastic Agents (chemical synthesis)
• Dicarboxylic Acids (chemistry)
• Fatty Acids, Unsaturated (chemical synthesis)
• Humans
• Plants, Medicinal (chemistry)
• Polyynes
• Stereoisomerism