(3S, 4R)-3, 4-Dihydroxy-N-alkyl-l-homoprolines: synthesis and computational mechanistic studies. Issue 47 (21st November 2019)

• Record Type: Journal Article
• Authors: Freitas, David S.; Sousa, Cristina E. A.; Parente, Joana; Drogalin, Artem; Gil Fortes, António; Cerqueira, Nuno M. F. S. A.; Alves, Maria J.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 47(2019)
• Page Start: 10052
• Page End: 10064
• Publication Date: 2019-11-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02141h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : This is the first synthetic report of (3 S, 4 R )-dihydroxy- N -alkyl-l -homoprolines described so far. Abstract : This is the first synthetic report of (3 S, 4 R )-dihydroxy- N -alkyl-l -homoprolines described so far. 2, 4- O -Benzylidene-d -erythrose was obtained from d -glucose with an improved yield, and then transformed into the title (3 S, 4 R )-dihydroxy- N -alkyl-l -homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the N H congener. The synthesis of final products from 1, 4-lactone intermediates was studied by computational means either under acidic or basic conditions. The theoretical mechanism studies fully explain the experimental results: (a) an equilibrium between l -homoprolines and their bicyclic counterparts is established in acids; (b) the equilibrium suffers a complete displacement towards the l -homoproline side in a basic medium.