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. 2011 Apr 20;133(15):5798-801.
doi: 10.1021/ja201834u. Epub 2011 Mar 29.

Total synthesis of N-methylwelwitindolinone D isonitrile

Vikram Bhat  1 , Kevin M Allan, Viresh H Rawal
Affiliations

Total synthesis of N-methylwelwitindolinone D isonitrile

Vikram Bhat et al. J Am Chem Soc. .

Abstract

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.

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Figures

Figure 1
Figure 1
Representative welwitindolinones
Scheme 1
Scheme 1
Retrosynthetic Analysis of 5
Scheme 2
Scheme 2
Synthesis of Coupling Fragments 9 and 10
Scheme 3
Scheme 3
Synthesis of Cyclization Precursor 8
Scheme 4
Scheme 4
Synthesis of Pentacycle 17
Scheme 5
Scheme 5
Synthesis of N-Methylwelwitindolinone D Isonitrile (5)
See this image and copyright information in PMC

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