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Total Syntheses of Kirkamide and N ‐acetyl ent ‐Conduramine B‐1
Author(s) -
Narayana Chintam,
Khanna Ashish,
Kumari Priti,
Sagar Ram
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000608
Subject(s) - enantiopure drug , chemistry , synthon , epoxide , aminocyclitol , regioselectivity , stereoselectivity , total synthesis , stereochemistry , ring (chemistry) , enantioselective synthesis , organic chemistry , catalysis , biochemistry , antibiotics , aminoglycoside
The second total synthesis of recently isolated new C 7 N aminocyclitol, kirkamide, has been developed. The enantiopure epoxide derived from N ‐acetylglucosamine in few steps was used as a synthon to accomplish the metal free synthesis of kirkamide and N ‐acetyl ent ‐conduramine B‐1 in gram scale. The key synthetic steps involve stereoselective epoxidation, acid mediated regioselective epoxide ring opening followed by selective olefination.