A New Enantioselective Approach to Total Synthesis of the Securinega Alkaloids: Application to (−)-Norsecurinine and Phyllanthine

Han, Gyoonhee; LaPorte, Matthew G.; Folmer, James J.; Werner, Kim M.; Weinreb, Steven M.

doi:10.1002/(sici)1521-3757(20000103)112:1<243::aid-ange243>3.0.co;2-6

Angewandte Chemie

2000

DOI: 10.1002/(sici)1521-3757(20000103)112:1<243::aid-ange243>3.0.co;2-6

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A New Enantioselective Approach to Total Synthesis of the Securinega Alkaloids: Application to (−)-Norsecurinine and Phyllanthine

Gyoonhee Han

Matthew G. LaPorte

James J. Folmer

et al.

Abstract: Ein preiswertes Prolinderivat und Chiralitätskontrolle spielen in der Totalsynthese der Securinega‐Alkaloide (−)‐Norsecurinin 1 und Phyllanthin 2 eine Rolle. Zu den Schlüsselschritten der Synthese von 1 gehören eine intramolekulare Ketonitrilkupplung und eine radikalchemische N‐Acylimin‐Bildung. Teil der Totalsynthese von 2 ist der stereoselektive Aufbau des Methoxypiperidinrings durch eine Imino‐Diels‐Alder‐Reaktion.

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Cited by 14 publications

References 28 publications

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Organoselenchemie in der stereoselektiven Synthese

Wirth

2000

Angewandte Chemie

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Reaktionen mit Selenreagentien haben in den vergangenen Jahren einen enormen Aufschwung erlebt, und die Chemie mit Selenverbindungen hat sich zu einem überaus nützlichen Werkzeug für Synthesechemiker entwickelt. Die Reaktivitäten selenhaltiger Verbindungen, die sich von denen schwefelhaltiger unterscheiden, haben zu interessanten neuen Synthesemethoden in der Organischen Chemie geführt. Verschiedene funktionelle Gruppen können selektiv und unter sehr milden Bedingungen in komplexe Moleküle eingeführt werden. In diesem Aufsatz werden die Prinzipien der Organoselenchemie im Hinblick auf die stereoselektive Synthese beleuchtet. Durch die einzigartigen Eigenschaften des Selens lassen sich neue und hoch selektive Transformationen entwickeln, die für die Synthese vielseitiger chiraler Synthesebausteine und zur Naturstoffsynthese genutzt werden können.

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Organoselenchemie in der stereoselektiven Synthese

Wirth

2000

Angewandte Chemie

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Organoselenium Chemistry in Stereoselective Reactions

Wirth

2000

Angew. Chem. Int. Ed.

297

188

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Selenium‐based methods have developed rapidly over the past few years asnd organoselenium chemistry has become a very useful tool in the hands of synthetic chemists. The different reactivity of selenium‐containing compounds in contrast to the sulfur analogues has led to versatile and new synthetic methods in organic chemistry. Various functionalities can be selectively introduced into complex molecules under very mild reaction conditions. In this review, the principles of organoselenium chemistry are traced back to their origins and are highlighted with respect to stereoselective synthesis. The unique properties of selenium allow the development of new and highly selective transformations, which can be employed subsequently in new routes for the synthesis of versatile chiral building blocks and for natural product synthesis.

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Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses

Wehlauch

Gademann

2017

Asian J Org Chem

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The Securinega alkaloids feature a compact tetracyclic structural framework and can be divided into four subclasses characterized by either a bridged [2.2.2]‐ or a [3.2.1]‐bicyclic core with two homologous series in each subclass. In the last two decades, many innovative strategies to chemically access the Securinega alkaloids have been developed. This Focus Review discusses the selected structures and syntheses of representative members of the Securinega alkaloids. Ring‐closing metathesis has enabled the syntheses of securinine and norsecurinine, and different cycloaddition approaches were key to the syntheses of nirurine and virosaines A and B. Virosine A was accessed through a Vilsmeier–Haack/Mannich reaction cascade. A bio‐inspired vinylogous Mannich reaction has enabled the synthesis of allosecurinine and this strategy has been extended by an intramolecular 1,6‐addition to obtain bubbialidine and secu′amamine E. A rearrangement process of the latter two alkaloids has furnished allonorsecurinine and allosecurinine, respectively. Finally, an expanded model for the biogenesis of the Securinega alkaloid subclasses is discussed.

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A New Enantioselective Approach to Total Synthesis of the Securinega Alkaloids: Application to (−)-Norsecurinine and Phyllanthine

Cited by 14 publications

References 28 publications

Organoselenchemie in der stereoselektiven Synthese

Organoselenchemie in der stereoselektiven Synthese

Organoselenium Chemistry in Stereoselective Reactions

Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses

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