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Optimized and Scalable Synthesis of Carba‐α‐ d ‐Glucosamine
Author(s) -
Babczyk Alexander,
Wingen Lukas M.,
Menche Dirk
Publication year - 2020
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.202001203
Subject(s) - chemistry , d glucosamine , glucosamine , protecting group , combinatorial chemistry , sequence (biology) , substrate (aquarium) , total synthesis , key (lock) , stereochemistry , nanotechnology , organic chemistry , biochemistry , computer science , alkyl , oceanography , computer security , geology , materials science
An efficient, high‐yielding synthesis of carba‐α‐ d ‐glucosamine is reported. Key features of this optimized route include an innovative protecting group strategy and an unusual, stereoconvergent Ferrier carbocyclization of a hindered substrate. The sequence enables the synthesis of larger amounts of this structurally novel antibiotic to allow more detailed biological evaluations of its unique mode of action.