Total Synthesis of N-Methylwelwitindolinone D Isonitrile

 

 

 

Vikram Bhat, Kevin M. Allan, and Viresh H. Rawal*

Described is a concise total synthesis of N-methylwelwitindolinone D isonitrile, the first in a family of complex bicyclo[4.3.1]decane-containing indole alkaloids to yield to synthesis. The complete carbon core of the natural product was assembled rapidly through a Lewis acid-mediated alkylative coupling followed directly by a palladium-catalyzed enolate arylation reaction. The final ring of the pentacycle was introduced by an indole oxidation/cyclization, and the isonitrile was installed through the rearrangement of an aldehyde to an isothiocyanate followed by desulfurization.

 

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 133: 15 (20 Apr. 2011): 5798-801.