Synthesis of the indeno[1,2-<i>b</i>]indole core of janthitrem B

Fresia, Marvin; Dierks, Alexandra; Jones, Peter G.; Lindel, Thomas

doi:10.1039/d3ob01566a

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob01566a

|View full text |Cite

Synthesis of the indeno[1,2-b]indole core of janthitrem B

Marvin Fresia,

Alexandra Dierks,

Peter G. Jones

et al.

Abstract: A novel synthetic route to a trans-fused indeno[1,2-b]indole proceeds via photo-Nazarov cyclization of a 3-acylindole precursor and stereospecific hydride shift at an in situ-formed dioxaphospholane.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Synthesis of Natural Product‐like Indeno[2,1‐b]indole/Shikimic Acid Hybrid Analogues with Anti‐osteoclastogenic Activity via Photo‐Nazarov Reaction

Shao,

Wang,

Zhang

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

Indeno[2,1‐b]indole and shikimic acid‐like structures are natural privileged scaffolds in several bioactive NPs. In this work, we developed a high‐efficient and diastereoselective synthetic approach to the construction of novel indeno[2,1‐b]indole/shikimic acid hybrid analogues via photo‐Nazarov reaction. The protocol is the first case of excited‐state photo‐Nazarov cyclization of indole‐2‐yl vinyl ketone to indeno[2,1‐b]indole. And the yield of (6aS, 10aR)‐product was up to 91% after the condition optimization. Even more attractive, several synthesized analogues exhibit potent RANKL‐induced osteoclastogenesis inhibitory activities, which suggests promising prospect of the novel indeno[2,1‐b]indole/shikimic acid hybrid scaffold for anti‐osteoporosis drug development.

show abstract

Synthesis of Natural Product‐like Indeno[2,1‐b]indole/Shikimic Acid Hybrid Analogues with Anti‐osteoclastogenic Activity via Photo‐Nazarov Reaction

Shao,

Wang,

Zhang

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis of the indeno[1,2-b]indole core of janthitrem B

Abstract: A novel synthetic route to a trans-fused indeno[1,2-b]indole proceeds via photo-Nazarov cyclization of a 3-acylindole precursor and stereospecific hydride shift at an in situ-formed dioxaphospholane.

Cited by 1 publication

References 30 publications

Synthesis of Natural Product‐like Indeno[2,1‐b]indole/Shikimic Acid Hybrid Analogues with Anti‐osteoclastogenic Activity via Photo‐Nazarov Reaction

Synthesis of Natural Product‐like Indeno[2,1‐b]indole/Shikimic Acid Hybrid Analogues with Anti‐osteoclastogenic Activity via Photo‐Nazarov Reaction

Contact Info

Product

Resources

About