α-Carbonyl radicals for total synthesis of natural products

Sha, Chin-Kang; Jean, T.-S.; Yau, Nei‐Tung; Huang, Shar-yin N.; Chiou, R.-T.; Young, J. F.; Lih, S.-H.; Tseng, Wen-Hung

doi:10.1351/pac199668030687

Pure and Applied Chemistry

1996

DOI: 10.1351/pac199668030687

|View full text |Cite

α-Carbonyl radicals for total synthesis of natural products

Chin-Kang Sha¹,

T.-S. Jean²,

Nei‐Tung Yau³

et al.

Abstract: Abstract

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1997

2023

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Photoredox‐Catalyzed Carbon Radical Generation from α‐Keto‐N,O‐acetals: Synthesis of Functionalized Azepino[1,2‐a]indoles and Azepino[1,2‐a]furo[3,2‐b]indoles

Seefeldt,

Villinger,

Brasholz

2023

Adv Synth Catal

View full text Add to dashboard Cite

C10a‐Acetoxylated perhydroazepino[1,2‐a]‐indoles, accessible via visible light‐mediated sensitized photooxygenation of cyclo‐hepta[b]indoles, are precursors to structurally elaborate carbon‐centered radicals. Their photoredox‐catalyzed SET reduction by phenothiazine or phenoxazine photocatalysts, followed by fragmentation and C−O bond cleavage, liberates tricyclic α‐amino‐α‐carbonyl radicals that readily engage in radical addition reactions with silyl enol ethers and silyl ketene acetals. The C−C functionalized azepinoindole[1,2‐a]indoles are useful building blocks for the synthesis of polycyclic indole derivatives as shown by the controlled borohydride reduction of a C10a‐methylenecarboxylate derivative, which leads stereoselectively to tetracyclic azepino[1,2‐a]furo[3,2‐b]indoles. The photocatalytic method developed herein is also suitable for the radical functionalization of simple α‐acetoxy acetophenones.

show abstract

Photoredox‐Catalyzed Carbon Radical Generation from α‐Keto‐N,O‐acetals: Synthesis of Functionalized Azepino[1,2‐a]indoles and Azepino[1,2‐a]furo[3,2‐b]indoles

Seefeldt,

Villinger,

Brasholz

2023

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Construction of Angularly Fused Tricyclic Compounds via Photo‐induced Radical Cascade Cyclization

Cao

Wang

et al. 2023

Chin. J. Chem.

View full text Add to dashboard Cite

Comprehensive SummaryPhoto‐induced electron transfer (PET) of silyl enol ethers has been employed to synthesize several fused ring systems. However, the method has limited applicability due to its narrow substrate scope, low product yields, unsatisfactory stereo‐ and regioselectivity. Herein, we report a PET‐triggered cascade reaction of silyl enolates that leads to the formation of angularly fused tricyclic scaffolds. The reaction exhibits broad substrate scope and excellent stereoselectivity. The regio‐ and stereoselectivity of this cascade reaction is elucidated via DFT calculation and conformational analysis.

show abstract

Synthesis of heterocycles by radical cyclisation

Aldabbagh¹,

Bowman²

1997

Contemp. Org. Synth.

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.

α-Carbonyl radicals for total synthesis of natural products

Abstract: Abstract

Cited by 3 publications

References 0 publications

Photoredox‐Catalyzed Carbon Radical Generation from α‐Keto‐N,O‐acetals: Synthesis of Functionalized Azepino[1,2‐a]indoles and Azepino[1,2‐a]furo[3,2‐b]indoles

Photoredox‐Catalyzed Carbon Radical Generation from α‐Keto‐N,O‐acetals: Synthesis of Functionalized Azepino[1,2‐a]indoles and Azepino[1,2‐a]furo[3,2‐b]indoles

Construction of Angularly Fused Tricyclic Compounds via Photo‐induced Radical Cascade Cyclization

Synthesis of heterocycles by radical cyclisation

Contact Info

Product

Resources

About