Advances in the Synthesis of Aryltetralin and Arylnaphthalene Lignans using Photocyclization

Lisiecki, Kamil; Czarnocki, Zbigniew

doi:10.1080/00304948.2018.1537239

Cited by 2 publications

(2 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Czarnocki et al applied their continuous-flow photocyclization methodology, previously used in the formal total synthesis of podophyllotoxin, to similar chiral bisbenzylidene succinates forming various cyclolignan analogues (Scheme ). ,, For the photocyclization, a different stereochemistry was found depending on the chiral auxiliary used and a different regioselectivity was observed depending on the substitution pattern of the benzylidene moiety adjacent to the ester group. Additionally, the total synthesis of (+)-epigalcatin was achieved with the flow photocyclization of a chiral atropisomeric 1,2-bisbenzylidene succinate amide ester as a key step.…”

Section: Flow Photochemistrymentioning

confidence: 99%

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

et al. 2021

View full text Add to dashboard Cite

Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing a plethora of opportunities to synthetic organic chemists. However, performing a photochemical transformation can be quite a challenge because of various issues related to the delivery of photons. These challenges have barred the widespread adoption of photochemical steps in the chemical industry. However, in the past decade, several technological innovations have led to more reproducible, selective, and scalable photoinduced reactions. Herein, we provide a comprehensive overview of these exciting technological advances, including flow chemistry, high-throughput experimentation, reactor design and scale-up, and the combination of photo- and electro-chemistry.

show abstract

Section: Flow Photochemistrymentioning

confidence: 99%

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

et al. 2021

View full text Add to dashboard Cite

show abstract

“…[7][8][9] Our research group is interested in the stereoselective synthesis of cyclolignans, achieved by photocyclization of chiral bis-benzylidenesuccinates. 10 We found that L-prolinol is an excellent chiral auxiliary 11 and used for the formal synthesis of PPT 12 and the total synthesis of (+)-epigalcatin. 13 We also studied the regioselectivity in the photocyclization of cyclolignan precursors 14 and we used the bis-benzylidenesuccinyl platform as a photolabile protecting group for secondary amines.…”

Section: Introductionmentioning

confidence: 95%

Unique cyclolignan’s architecture obtained via acid catalyzed cyclization/intramolecular Friedel-Crafts tandem reaction

Krawczyk¹,

Lisiecki²,

Czarnocki³

2020

Arkivoc

Self Cite

View full text Add to dashboard Cite

We examine the cyclization of chiral bis-benzylidenesuccinate 6 (precursor to podophyllotoxin-related cyclolignans) in different conditions. Under acid catalysis, a new type of cyclolignan was obtained via cyclization/intramolecular Friedel-Crafts tandem reaction. The structure of the product was confirmed by spectroscopic data and X-ray diffraction. Also, a plausible mechanism of this transformation was proposed.

show abstract

Advances in the Synthesis of Aryltetralin and Arylnaphthalene Lignans using Photocyclization

Cited by 2 publications

References 43 publications

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Unique cyclolignan’s architecture obtained via acid catalyzed cyclization/intramolecular Friedel-Crafts tandem reaction

Contact Info

Product

Resources

About