@article{9b767dbac4fc4890932d486d6fb1c428,
title = "A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C",
abstract = "The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds. Here, we report a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxylsvianucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps). The developed method is operationally simple and demonstrates broad scope in terms of nucleophile identity and indole substitution, tolerating 2-alkyl substituents and free indole N-H groups, elements beyond the scope of most prior approaches. Spirocyclic indoxyl products are also accessibleviaintramolecular nucleophilic trapping.",
author = "Fan Xu and Smith, {Myles W.}",
note = "Funding Information: This work was financially supported by UT Southwestern through the W. W. Caruth Jr. Scholarship and the Welch Foundation (I-2045). We thank the Tambar, Ready, Qin, DeBrabander, Chen, and Falck groups (UT Southwestern) for generous access to equipment and chemicals, as well as helpful discussions. We are grateful to Dr Feng Lin, Dr Eric Weaver (UT Arlington), and Dr Vincent Lynch (UT Austin) for assistance with NMR studies, high-resolution mass spectrometry, and X-ray crystallographic analysis, respectively. Funding Information: This work was nancially supported by UT Southwestern through the W. W. Caruth Jr. Scholarship and the Welch Foundation (I-2045). We thank the Tambar, Ready, Qin, DeBrabander, Chen, and Falck groups (UT Southwestern) for generous access to equipment and chemicals, as well as helpful discussions. We are grateful to Dr Feng Lin, Dr Eric Weaver (UT Arlington), and Dr Vincent Lynch (UT Austin) for assistance with NMR studies, high-resolution mass spectrometry, and X-ray crystallographic analysis, respectively. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",
year = "2021",
month = nov,
day = "7",
doi = "10.1039/d1sc03533a",
language = "English (US)",
volume = "12",
pages = "13756--13763",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "41",
}