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Synthesis of Chiral Tetrahydrofuran Building Blocks from Pantolactones: Application in the Synthesis of Empagliflozin and Amprenavir Analogs
Author(s) -
Athawale Paresh R.,
Kumari Neeta,
Dandawate Monica R.,
Kashinath K.,
Srinivasa Reddy D.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900718
Subject(s) - chemistry , empagliflozin , amprenavir , tetrahydrofuran , enantioselective synthesis , combinatorial chemistry , stereochemistry , organic chemistry , protease , enzyme , catalysis , hiv 1 protease , medicine , endocrinology , solvent , diabetes mellitus , type 2 diabetes mellitus
Chiral 4,4–dimethyl tetrahydrofuran (THF) derivatives were synthesized from commercially available D‐(–)/ l ‐(+) pantolactones, which can serve as chiral building blocks in medicinal chemistry. In addition, two of the synthesized building blocks were utilized for the synthesis of new amprenavir (HIV protease inhibitor) and empagliflozin (anti‐diabetic) analogs. The synthesized analogs may have beneficial effects in terms of pharmacokinetics and modulation of bioactivity.