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Flexible Total Synthesis of 11‐Deoxylandomycins and Their Non‐Natural Analogues by Way of Asymmetric Metal Catalysis
Author(s) -
Lee Juyeol,
Kang Jihun,
Lee Sukhyun,
Rhee Young Ho
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913706
Subject(s) - total synthesis , catalysis , natural (archaeology) , enantioselective synthesis , chemistry , feature (linguistics) , signature (topology) , combinatorial chemistry , alcohol , stereochemistry , computer science , organic chemistry , mathematics , biology , philosophy , paleontology , linguistics , geometry
A de novo first collective total synthesis of 11‐deoxylandomycins is reported. A signature step is featured by the Pd‐catalyzed asymmetric addition of alcohol to ene‐alkoxyallenes that assembles oligomeric 2,3,6‐trideoxyoligosaccharides. The unique feature of the protocol is illustrated by a flexible access to various natural 11‐deoxylandomycins as well as non‐natural analogues.