Heterocyclic Synthesis via the Tandem Thionium/<i>N</i>-Acyliminium Ion Cascade

Padwa, Albert; Heidelbaugh, Todd M.; Kuethe, Jeffrey T.; McClure, Michael S.

doi:10.1021/jo981349w

Cited by 43 publications

(32 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Tetracyclic scaffold 292 was obtained as a racemic mixture in more than 90% yield in the presence of TFA or TfOH. Compounds 294 were obtained as the exclusive racemic products through a Pummerer/Pictet–Spengler cyclization sequence, following treatment with trifluoroacetic anhydride and TFA. The comparatively low yield of 294b was explained by the entropically more demanding cyclization toward the seven-membered ring .…”

Section: Synthesis Of Tetracyclic Scaffoldsmentioning

confidence: 99%

Scaffold Diversity from N-Acyliminium Ions

Nielsen

2017

Chem. Rev.

171

View full text Add to dashboard Cite

N-Acyliminium ions are powerful reactive species for the formation of carbon-carbon and carbon-heteroatom bonds. Strategies relying on intramolecular reactions of N-acyliminium intermediates, also referred to as N-acyliminium ion cyclization reactions, have been employed for the construction of structurally diverse scaffolds, ranging from simple bicyclic skeletons to complex polycyclic systems and natural-product-like compounds. This review aims to provide an overview of cyclization reactions of N-acyliminium ions derived from various precursors for the assembly of structurally diverse scaffolds, covering the literature over the past 12 years (from 2004 to 2015).

show abstract

Section: Synthesis Of Tetracyclic Scaffoldsmentioning

confidence: 99%

Scaffold Diversity from N-Acyliminium Ions

Nielsen

2017

Chem. Rev.

171

View full text Add to dashboard Cite

show abstract

“…The Padwa group has employed a Pummerer/Pictet–Spengler cascade reaction,95–97 involving both thionium and iminium ion intermediates, in the preparation of the alkaloid jamtine ( 191 , Scheme 28) 98. This synthesis also serves to demonstrate the versatility of sulfoxides in total synthesis.…”

Section: Electrophilic Cascadesmentioning

confidence: 99%

Cascade Reactions in Total Synthesis

2006

View full text Add to dashboard Cite

The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.

show abstract

“…Padwa et al nutzten zur Synthese des Alkaloids Jamtin ( 191 ) eine Kaskade aus Pummerer‐ und Pictet‐Spengler‐Reaktion95–97 (Schema 28), an der sowohl Thionium‐ als auch Iminium‐Intermediate beteiligt sind 98. Diese Methode veranschaulicht auch die Vielseitigkeit von Sulfoxiden in der Totalsynthese.…”

Section: Elektrophile Kaskadenunclassified

Kaskadenreaktionen in der Totalsynthese

2006

View full text Add to dashboard Cite

Die Entwicklung und Umsetzung von Kaskadenreaktionen hat zu beachtlichen neuartigen, eleganten und effizienten Synthesestrategien geführt. Als besonders anspruchsvoll erwies sich die Anwendung von Kaskadenreaktionen in der Naturstoffsynthese, doch gerade hier winken verblüffende und zugleich aufschlussreiche Ergebnisse als Belohnung. In diesem Aufsatz werden ausgewählte Kaskadenreaktionen in der Totalsynthese erläutert, wobei neuere Anwendungen besonders hervorgehoben werden. Die erörterten Beispiele sollen die Leistungsfähigkeit dieser Prozesse beim Aufbau von komplexen Molekülstrukturen veranschaulichen und ihr Potenzial für zukünftige chemische Synthesen verdeutlichen.

show abstract

Heterocyclic Synthesis via the Tandem Thionium/N-Acyliminium Ion Cascade

Cited by 43 publications

References 19 publications

Scaffold Diversity from N-Acyliminium Ions

Scaffold Diversity from N-Acyliminium Ions

Cascade Reactions in Total Synthesis

Kaskadenreaktionen in der Totalsynthese

Contact Info

Product

Resources

About