Journal
TETRAHEDRON
Volume 76, Issue 51, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131181
Keywords
Solid-state photochemistry; Natural products; Vicinal quaternary centers; Prenylation
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Funding
- National Science Foundation [CHE-1855342]
- UCLA Graduate Division
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
- Trueblood Family
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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. (C) 2020 Elsevier Ltd. All rights reserved.
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