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. 2010 Jun 4;12(11):2492-5.
doi: 10.1021/ol1006373.

Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core

Richard W Heidebrecht Jr  1 , Brian Gulledge, Stephen F Martin
Affiliations

Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core

Richard W Heidebrecht Jr et al. Org Lett. .

Abstract

The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.

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Figures

Figure 1
Figure 1
Structures of Welwitindolinone A Isocyanate (1), Welwitindolinone A Isothiocyanate (2) and N-Methylwelwitinolidone C Isothiocyanate (3).
Scheme 1
Scheme 1
Initial Retrosynthetic Proposal
Scheme 2
Scheme 2
Preparation of Ketoester 6
Scheme 3
Scheme 3
Attempted Preparation of Tetracycle 15
Scheme 4
Scheme 4
Attempted Preparation of an Indolic Tetracycle
Scheme 5
Scheme 5
A Revised Retrosynthetic Analysis
Scheme 6
Scheme 6
Preparation of Vinylogous Silyl Ketene Acetal 22.
Scheme 7
Scheme 7
Preparation of the Welwitindolinone C Skeleton
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