Issue 3, 2024

A de novo synthesis of the bisindole alkaloid geissolosimine: collective synthesis of geissoschizoline, akuammicine, (16S)-deshydroxymethylstemmadenine and Aspidospermatan alkaloids

Abstract

In this study, we accomplished a de novo synthesis of the bisindole alkaloid geissolosimine. Geissoschizoline, the north fragment of geissolosimine, was first prepared in 15 steps (longest linear sequence, LLS) by leveraging a catalytic asymmetric double Michael addition, which also highlights a domino oxidation/intramolecular condensation and an unprecedented SnCl4/TFA-promoted deprotection/isomerization/intramolecular cyclization cascade. The biomimetic union of geissoschizoline with vellosimine was successively realized under the influence of (±)-CSA, enabling the synthesis of geissolosimine. Additionally, this innovative strategy also provides concise access to akuammicine and the bio-inspired transformation of akuammicine via (16S)-deshydroxymethylstemmadenine to condylocarpine and iso-condylocarpine was also demonstrated.

Graphical abstract: A de novo synthesis of the bisindole alkaloid geissolosimine: collective synthesis of geissoschizoline, akuammicine, (16S)-deshydroxymethylstemmadenine and Aspidospermatan alkaloids

Supplementary files

Article information

Article type
Research Article
Submitted
14 Nov 2023
Accepted
04 Dec 2023
First published
04 Dec 2023

Org. Chem. Front., 2024,11, 703-708

A de novo synthesis of the bisindole alkaloid geissolosimine: collective synthesis of geissoschizoline, akuammicine, (16S)-deshydroxymethylstemmadenine and Aspidospermatan alkaloids

J. Yan, Y. Zhen, P. Wang, Y. Han, H. Zou, J. Chen, W. He and W. Xie, Org. Chem. Front., 2024, 11, 703 DOI: 10.1039/D3QO01898A

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