Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O–H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition. [Display omitted]

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Veröffentlicht in:Tetrahedron 2010-08, Vol.66 (33), p.6647-6655
Hauptverfasser: Freeman, David B., Holubec, Alexandra A., Weiss, Matthew W., Dixon, Julie A., Kakefuda, Akio, Ohtsuka, Masami, Inoue, Munenori, Vaswani, Rishi G., Ohki, Hidenori, Doan, Brian D., Reisman, Sarah E., Stoltz, Brian M., Day, Joshua J., Tao, Ran N., Dieterich, Noah A., Wood, John L.
Format: Artikel
Sprache:eng
Schlagworte:
[3+2] Dipolar cycloaddition
Chloronium-ion semi-pinacol
O–H insertion
Rhodium carbenoid
Welwitindolinone
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Zusammenfassung:Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O–H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.04.131