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Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy

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Abstract

A total synthesis to the pseudoaspidospermidine family via a C–H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C–H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.

Graphical abstract: Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy

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Publication details

The article was received on 07 Apr 2017, accepted on 15 May 2017 and first published on 19 May 2017


Article type: Communication
DOI: 10.1039/C7CC02699D
Citation: Chem. Commun., 2017, Advance Article
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    Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy

    C. Leitner and T. Gaich, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02699D

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