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Synthesis of Dysoxylactam A Using Iterative Homologation of Boronic Esters
Author(s) -
Rogers Jack J.,
Aggarwal Varinder K.
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.202100413
Subject(s) - chemistry , borylation , sequence (biology) , total synthesis , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , aryl
Dysoxylactam A is a 17‐membered macrocyclic lipid which has been found to dramatically reverse multidrug resistance in cancer cells. Three previous syntheses have been reported in 15–17 steps. Using iterative lithiation‐borylation reactions as the key C−C bond forming and stereocontrolling steps, we now describe an 11‐step synthesis of dysoxylactam A. The complete sequence only required a total of five chromatographic purifications and used minimal protecting groups making it both rapid and efficient.