Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A–E, G, Q and their analogues. Issue 34 (15th August 2018)

• Record Type: Journal Article
• Authors: Manchoju, Amarender; Annadate, Ritesh A.; Desquien, Lise; Pansare, Sunil V.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 34(2018)
• Page Start: 6224
• Page End: 6238
• Publication Date: 2018-08-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01511b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Diastereoselective aldol condensation of diazotetronic acid and a subsequent arene C–H insertion provides an efficient route to the aspulvinone motif. Abstract : A modular synthesis of aspulvinones A, B, C, D, E, G and the recently isolated aspulvinone Q was developed. The methodology features a highly stereoselective aldol condensation of diazotetronic acid with aldehydes to provide 5-arylidene diazotetronates. Subsequent catalytic intermolecular C–H insertion reactions of the arylidene tetronates with arenes provide a series of naturally occurring aspulvinones including aspulvinones C, D and Q which have not been synthesized before. Variation of the aldehyde and the arene components furnishes synthetic analogues of the aspulvinones.