Angew Chem Int Ed Engl August 2020 PMID 32415682

TiCl -Mediated Synthesis of 2,3,3-Trisubstituted Indolenines: Total Synthesis of (+)-1,2-Dehydroaspidospermidine, (+)-Condyfoline, and (-)-Tubifoline.

Bastien Delayre, Cyril Piemontesi, Qian Wang, Jieping Zhu

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Peak: 6 in Jun 2020

across 2 sources since Jun 2020

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What people are saying

Several discussions highlight the innovative use of TiCl3 in synthesizing complex indolenines, with phrases like 'groundbreaking method' and 'versatile approach' conveying high interest. Users also discuss mechanistic aspects and real-world applications, reflecting deep engagement and recognition of the publication’s potential impact in advancing synthetic chemistry.

AgreementModerate agreement

Most posts recognize and support the significance of the new synthesis method and its application to complex natural products.

InterestHigh interest

Discussions reflect high curiosity and enthusiasm, especially regarding the novel methods and their implications.

EngagementModerate engagement

Posts reference specific reactions, steps involved, and potential applications, indicating meaningful participation.

ImpactHigh impact

The detailed analysis and focus on the method's versatility suggest that users see this work as influential in the field of organic synthesis.

Abstract in brief

This study introduces a new method to synthesize a specific type of indolenine compound using a titanium chloride (TiCl) mediated reduction and cyclization process, which is important because these compounds are found in many biologically active alkaloids.
The researchers demonstrated the effectiveness of this method by completing the total synthesis of two complex natural products, 12-dehydroaspidospermidine and condyfoline, showing that the reaction is versatile and can be applied to different molecules.
The process involves a series of steps, including reduction of nitro groups, electrocyclization, and alkyl shifts, which follow a specific concerted pathway, offering mechanistic insights and enabling efficient conversion of condyfoline to tubifoline through a cyclization cascade.

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