Asymmetric total synthesis of dihydroisocoumarins: 6-methoxymellein, kigelin and fusarentin 6, 7 dimethyl ether by employing proline catalysed asymmetric α-aminoxylation. Issue 46 (13th November 2020)

• Record Type: Journal Article
• Authors: Markad, Sachin B.; Mane, Baliram B.; Waghmode, Suresh B.
• Is Part Of: Tetrahedron. Volume 76:Issue 46(2020)
• Publication Date: 2020-11-13
• Subjects: Dihydroisocoumarins -- Organocatalyst -- α-aminoxylation -- HWE olefination -- Oxa-Pictet-Spengler cyclisation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131524
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A concise asymmetric total synthesis of dihydroisocoumarins such as 6-methoxymellein, kigelin and fusarentin 6, 7-dimethyl ether in high enantiopurity have been achieved from non-chiral aldehydes by employing proline catalysed asymmetric α-aminoxylation reaction. The required stereochemistry of hydroxyl group have been generated by alternating L or D proline as a organocatalyst in α-aminoxylation step and lactone ring is assembled by oxa-Pictet-Spengler cyclisation reaction as the key steps. Graphical abstract: Image 1 Highlights: A concise total synthesis of dihydroisocoumarins. High enantiopurity. Proline catalysed asymmetric α-aminoxylation reaction.