Total Synthesis of (−)-N-Methylwelwitindolinone C Isothiocyanate

We report the first total synthesis of (−)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bri...

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Published in:Journal of the American Chemical Society 2011-10, Vol.133 (40), p.15797-15799
Main Authors: Huters, Alexander D, Quasdorf, Kyle W, Styduhar, Evan D, Garg, Neil K
Format: Article
Language:English
Subjects:
Chemistry Techniques, Synthetic
Cyanobacteria - chemistry
Cyclization
Indole Alkaloids - chemical synthesis
Indoles - chemical synthesis
Indoles - chemistry
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a470t-b131fb53fb0e1883abc258d042d9fd9061f27c75c9e00ae9c52bc24bb3090633
cites cdi_FETCH-LOGICAL-a470t-b131fb53fb0e1883abc258d042d9fd9061f27c75c9e00ae9c52bc24bb3090633
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creator Huters, Alexander D
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Styduhar, Evan D
Garg, Neil K
description We report the first total synthesis of (−)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.
doi_str_mv 10.1021/ja206538k
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Chemistry Techniques, Synthetic
Cyanobacteria - chemistry
Cyclization
Indole Alkaloids - chemical synthesis
Indoles - chemical synthesis
Indoles - chemistry
Stereoisomerism
title Total Synthesis of (−)-N-Methylwelwitindolinone C Isothiocyanate
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