144542-72-3Relevant articles and documents
Total Synthesis of the Bacterial Diisonitrile Chalkophore SF2768
Xu, Yao,Tan, Derek S.
supporting information, p. 8731 - 8735 (2019/11/03)
Chalkophores are bacterial natural products that chelate and transport extracellular copper. The diisonitrile natural product SF2768 was first isolated from a Streptomyces species as an antifungal antibiotic and has more recently been characterized as a bacterial chalkophore and potential virulence factor. Herein, we report a modular synthesis of SF2768 and related acyclic analogues, allowing assignment of syn-stereochemistry across the central lactol ring. The copper-binding properties of these diisonitriles have also been studied.
Asymmetric syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids. Studies directed to the design of novel substrate-based inhibitors of L,L-diaminopimelate epimerase
Williams, Robert M.,Fegley, Glenn J.,Gallegos, Renee,Schaefer, Felicity,Pruess, David L.
, p. 1149 - 1164 (2007/10/03)
The asymmetric syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids (7a-c) is described. The synthesis features phosphonate coupling of 13 and 14 to form the corresponding E-olefins which are subsequently cyclopropanated and deprotected under dissolving metal conditions.
