Puzzling Out the Structure of Novofumigatamide: Total Synthesis of Constitutional Isomers. Part II.

ABSTRACT: The total synthesis of several constitutional isomers showing a different connectivity of the macrolactam ring with the hexahydropyrrolo[2,3-b]indole core, as well as those arising from the positional exchange of the valine and the anthranilate units of the structure originally proposed for (-)-novofumigatamide, has been carried out. The constitutional isomers with 12-membered ring macrolactam connected with the pyrroloindoline framework through the indole nitrogen, and the acetyl group at the pyrrole nitrogen, of endo relative configuration, were prepared through the condensation between the tryptophan and valine edges derived from l- or d-tryptophan and l-valine amino acids. The corresponding exo products are highly unstable structures difficult to isolate and charac

SUBMITTER: Garcia-Dominguez P 

PROVIDER: S-EPMC9552235 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature