Evaluation of the photodecarbonylation of crystalline ketones for the installation of reverse prenyl groups on the pyrrolidinoindoline scaffold.

ABSTRACT: We report synthetic efforts toward the regiocontrolled installation of the prenyl moiety in debromoflustramine A by the regiospecific photodecarbonylation of a prenyl-substituted ketone. Synthetic approaches to access the plausible photodecarbonylation substrates beginning from tryptamine were evaluated. Initial attempts to synthesize a suitable substrate for photodecarbonylation were hampered by a lack of substrate crystallinity (a prerequisite for solid-state photochemistry). Ultimately, a crystalline substrate could be accessed to attempt the key step by judicious selection of N-substituents. Although the photodecarbonylation did not result in the desired reverse prenylation, this study highlights the troubleshooting and optimization required for crystal phase photochemistry and undersc

SUBMITTER: Dotson JJ 

PROVIDER: S-EPMC8657873 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature