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A novel total synthesis of the bioactive poly-substituted carbazole alkaloid carbazomadurin A

✍ Scribed by Yuhzo Hieda; Tominari Choshi; Sayuri Kishida; Haruto Fujioka; Satoshi Hibino

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
344 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new total synthesis of the neuronal cell-protecting carbazole alkaloid carbazomadurin A is described. The key step was an allene-mediated electrocyclic reaction involving an indole [b]-bond for the construction of a highly substituted carbazole ring. The E-alkenyl side chain at the C1 position of carbazole was introduced between O-triflate and alkenyl pinacol borate using the Suzuki-Miyaura reaction. SEM groups were cleaved with TBAF and the formyl group was reduced to provide carbazomadurin A.

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