DATE2024.09.19 #Press Releases
Shining light on the synthesis of indole alkaloids!
――Innovative photochemical flow approach for constructing complex polycyclic scaffolds――
Summary
Gavin Tay (graduate student), Soushi Nishimura (graduate student at the time), and Professor Hiroki Oguri from the Graduate School of Science at the University of Tokyo pioneered a photo-flow process for the efficient construction of alkaloidal scaffolds as potential drug candidates. In this study, they designed a moderately stabilized multipotent intermediate 2 from the hypothetical biosynthetic intermediate dehydrosecodine 1 and developed an innovative synthetic method to construct an iboga-type tetracyclic scaffold 3 that could not be synthesized by conventional thermal activation. They established a straightforward micro-flow photochemical process without the need for additional photocatalysts or photosensitizers, demonstrating high efficiency in the rarely reported photochemical [4+2] cycloaddition reaction and broad substrate applicability. Furthermore, by precisely turning the electron densities and conformations of the dehydrosecodine-type intermediates, they efficiently achieved light-induced [2+2] cycloaddition reactions, facilitating the streamlined synthesis of novel pentacyclic scaffolds 4 and 5 that are otherwise challenging to access via biosynthetic pathways.
Figure：Photochemical flow synthesis process for constructing complex multicyclic alkaloidal scaffolds.
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Journals
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Journal name Chemical Science Title of paper