An Enantiospecific Synthesis of Isoneoamphilectane Confirms Its Strained Tricyclic Structure.

ABSTRACT: We describe a total synthesis of the rare isocyanoterpene natural product isoneoamphilectane and two of its unnatural diastereomers. The significantly strained ring system of the reported natural product─along with a hypothesis about a biosynthetic relationship to related family members─inspired us to consider a potential misassignment in the structure's relative configuration. As a result, we initially targeted two less strained, more accessible, stereoisomers of the reported natural product. When these compounds failed to exhibit spectroscopic data that matched those of isoneoamphilectane, we embarked on a synthesis of the originally proposed strained structure via an approach that hinged on a challenging cis-to-trans decalone epimerization. Ultimately, we implemented a nov

SUBMITTER: Dwulet NC 

PROVIDER: S-EPMC9936588 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature