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

文献情報

出版日 2023-12-04

DOI 10.1039/D3QO01898A

インパクトファクター 5.281

著者

Jiahang Yan, Yanxia Zhen, Pengyan Wang, Yimeng Han, Huanhuan Zou, Junhan Chen, Weigang He

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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