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

Autor: Dotson JJ; University of California, Los Angeles, Department of Chemistry and Biochemistry, Los Angeles, CA, 90095, USA., Garg NK; University of California, Los Angeles, Department of Chemistry and Biochemistry, Los Angeles, CA, 90095, USA., Garcia-Garibay MA; University of California, Los Angeles, Department of Chemistry and Biochemistry, Los Angeles, CA, 90095, USA.
Jazyk: angličtina
Zdroj: Tetrahedron [Tetrahedron] 2020 Dec; Vol. 76 (51). Date of Electronic Publication: 2020 Apr 10.
DOI: 10.1016/j.tet.2020.131181
Abstrakt: 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 underscores methods that can be used to control substrate crystallinity.
Competing Interests: Declaration of interests The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Databáze: MEDLINE
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