Advances and Strategies towards Synthesis of Aspidosperma Indole Alkaloids Goniomitine

Goniomitine is of the aspidosperma alkaloid family, with an angularly fused tetracyclic skeleton housing an all‐carbon quaternary carbon chiral center alongside an aminal functional group. This natural product has garnered attention as a synthetic target due to its intriguing molecular architecture...

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Bibliographic Details
Published in:Chemistry & biodiversity 2024-06, Vol.21 (6), p.e202400416-n/a
Main Author: Ji, Cong‐Bin
Format: Article
Language:English
Subjects:
Alkaloids
Aspidosperma - chemistry
Carbon
Cyclization
Cyclization Reaction
Functional groups
Goniomitine
Indole Alkaloid
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Indole Alkaloids - pharmacology
Indoles
Molecular Structure
Natural product
Natural products
Oxidation
Oxidation-Reduction
Stereoisomerism
Synthesis
Total synthesis
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Summary:Goniomitine is of the aspidosperma alkaloid family, with an angularly fused tetracyclic skeleton housing an all‐carbon quaternary carbon chiral center alongside an aminal functional group. This natural product has garnered attention as a synthetic target due to its intriguing molecular architecture and anti‐proliferative activity in recent years. Following the first synthesis of (−)‐goniomitine by Takano in 1991, synthetic chemists have developed various methods. This review provides an overview of the methodologies used in the synthesis of goniomitine in racemic and enantiopure forms via divergent construction indole framework, indole functionalization, and the integrated oxidation/reduction/cyclization (iORC) sequence from 1991 to 2023.
ISSN:1612-1872
1612-1880
1612-1880
DOI:10.1002/cbdv.202400416