Journal
TETRAHEDRON
Volume 74, Issue 26, Pages 3246-3252Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.04.053
Keywords
Radical chemistry; Photocatalysis; Natural products
Categories
Funding
- Boston University Undergraduate Research Opportunities Program
- NIH-NIGMS [R01-GM096129]
- Camille Dreyfus Scholar Award Program
- Eli Lilly
- Novartis
- Boston University
- University of Michigan
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The use of lithium bis-catechol borate (LiB(cat)(2)) as a reductive quencher for the photoredox mediated intermolecular CH functionalization of various heteroaromatics with bromopyrroloindolines is described. LiB(cat)(2) offers a financial benefit over state-of-the-art quenchers currently in use while eliminating the side reactions that typically plague these couplings. The advantage of this methodology is highlighted by the synthesis of C3-C2' (-) gliocladin C. Furthermore, additional examples of reactivity with various bromopyrroloindolines sets the stage for expedient routes towards other pharmaceutically active hexahydropyrroloindoline alkaloids and their analogues. (C) 2018 Elsevier Ltd. All rights reserved.
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