Tsuji-Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines
Demillo, Violeta G
Jones, Dylan E
Lumangtad, Liezel A
Pflug, Nicholas C
Scarbrough, Emily D
Bell, Thomas W
AffiliationUniv Arizona, BIO5 Inst
MetadataShow full item record
PublisherAMER CHEMICAL SOC
CitationACS Omega 2019, 4, 1254−1264
RightsCopyright © 2019 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
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AbstractMacrocyclic triamine disulfonamides can be synthesized by double Tsuji-Trost N-allylation reaction of open-chain disulfonamides with 2-alkylidene-1,3-propanediyl bis(carbonates). The previously used Atkins-Richman macrocyclization method generally gives lower yields and requires more tedious purification of the product. Solvent, palladium source, ligand, and concentration have all been varied to optimize the yields of two key 12-membered ring bioactive compounds, CADA and VGD020. The new approach tolerates a wide range of functional groups and gives highest yields for symmetrical compounds in which the acidities of the two sulfonamide groups are matched, although the yields of unsymmetrical compounds are still generally good. The method has also been extended to the synthesis of 11-membered rings, pyridine-fused macrocycles, and products bearing an ester or aryl substituent on the exocyclic double bond.
NoteOpen access journal
VersionFinal published version
SponsorsNIH [1R15 GM120659-01]
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