Gold-catalyzed homo- and cross-annulation of alkynyl carboxylic acids: a facile access to substituted 4-hydroxy 2H-pyrones and total synthesis of pseudopyronine A. Issue 42 (22nd October 2020)

• Record Type: Journal Article
• Authors: Gayyur, ; Choudhary, Shivani; Saxena, Anchal; Ghosh, Nayan
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 42(2020)
• Page Start: 8716
• Page End: 8723
• Publication Date: 2020-10-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01700k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A single-step protocol for the synthesis of 3, 6-disubstituted 4-hydroxy 2 H -pyrones under goldcatalyzed conditions is developed from alkynyl acids. The total synthesis of pseudopyronine A is achieved with an overall 24% yield. Abstract : A Au(i )-catalyzed homo- and cross-annulation reaction of alkynyl carboxylic acids offering 3, 6-disubstituted 4-hydroxy 2 H -pyrones has been demonstrated. The reaction tolerates various substituted alkynyl carboxylic acids and moderate to good yields of α-pyrone scaffolds have been observed. Later, a gram-scale reaction of the acid and the total synthesis of the natural product pseudopyronine A have been carried out successfully.