Total Synthesis of (±)‐Lysergic Acid by an Intramolecular Imino‐<i>Diels</i>‐<i>Alder</i> Reaction. Preliminary communication

Oppolzer, Wolfgang; Francotte, Eric; Bättig, Kurt

doi:10.1002/hlca.19810640212

Cited by 94 publications

(22 citation statements)

References 29 publications

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“…Significantly, Oppolzer and Robbiani optimized this cyclobutene‐opening methodology72b to achieve greatly enhanced yields of 143 . They also further extended this insightful Diels–Alder approach to heterocyclic systems by using tethered imines as substrates, thus paving the way for a plethora of subsequent applications 73…”

Section: Diels–alder Reactions In Disguise: Cloaked Dienes and Dienop...mentioning

confidence: 99%

The Diels-Alder Reaction in Total Synthesis

Nicolaou

Snyder

Montagnon

et al. 2002

Angew. Chem. Int. Ed.

1,716

778

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The Diels–Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels–Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.

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Section: Diels–alder Reactions In Disguise: Cloaked Dienes and Dienop...mentioning

confidence: 99%

The Diels-Alder Reaction in Total Synthesis

Nicolaou

Snyder

Montagnon

et al. 2002

Angew. Chem. Int. Ed.

1,716

778

View full text Add to dashboard Cite

show abstract

“…Das Erhitzen von 141 in siedendem o ‐Xylol führte wie erwartet zu einer reversiblen, konrotatorischen Ringöffnung unter Bildung des hochreaktiven o ‐Chinodimethans 142 , welches anschließend durch eine geplante Diels‐Alder‐Reaktion mit der benachbarten Alkin‐Einheit das polycyclische Systems 143 mit 73 % Ausbeute als Vorläufer für den anvisierten Naturstoff lieferte. Oppolzer und Robbiani optimierten die Cyclobuten‐Ringöffnungsmethode,72b und konnten somit nicht nur deutlich verbesserte Ausbeuten sicherstellen, sondern die Methode auch auf die Herstellung heterocyclischer Systeme unter Verwendung von Iminen erweitern, womit der Weg zu einer Vielzahl späterer Anwendungen geebnet wurde 73…”

Section: Versteckte Diels‐alder‐reaktionen: Maskierte Diene Und Dieno...unclassified

Die Diels-Alder-Reaktion in der Totalsynthese

et al. 2002

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In den letzten Jahrzehnten hat wohl keine andere Reaktion das Forschungsgebiet der Totalsynthese mehr geprägt als die Diels‐Alder‐Reaktion. Mit einer Vielzahl von Anwendungen dieser großartigen pericyclischen Reaktion, oftmals als entscheidendes Element einer eleganten Kaskadenreaktion zur Herstellung komplexer Molekülstrukturen, ermöglichte die Diels‐Alder‐Cycloaddition die Lösung einer Reihe unterschiedlicher, von der Natur in Form von Naturstoffen gestellter Syntheseprobleme. Zur Feier des hundertjährigen Jubiläums von Alders Geburtstag soll dieser Aufsatz die ungemeine Leistungsfähigkeit der von ihm entdeckten Reaktion anhand ausgewählter Beispiele im Kontext der Totalsynthese verdeutlichen und ihre Vielseitigkeit sowie ihr gewaltiges, noch immer nicht vollständig erfasstes Potential unterstreichen.

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“…They also further extended this insightful Diels ± Alder approach to heterocyclic systems by using tethered imines as substrates, thus paving the way for a plethora of subsequent applications. [73] A related and equally spectacular application of the intramolecular Diels ± Alder reaction of benzocyclobutenegenerated o-quinodimethanes is demonstrated in the total synthesis of estrone (150, Scheme 22) [74] during the conversion of 147 into the steroidal skeleton 149 by Vollhardt and coworkers. [75] Apart from this particular transformation, however, this elegant synthesis includes an additional tantalizing Scheme 22.…”

Section: Diels ± Alder Reactions In Disguise: Cloaked Dienes and Dien...mentioning

confidence: 99%

Professor K. C. Nicolaou*Department of Chemistry, The Scripps Research Institute and the University of California, San Diego, 10550 North Torrey Pines Road, La Jolla, California 92037 USA.

Nicolaou¹

2002

J. Chem. Soc., Perkin Trans. 1

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After numerous near-discoveries of the [42] cycloaddition reaction by several luminaries in the field of organic chemistry during the early part of the 20th century, [1,2] the keen insight of Professor Otto Diels [3] and his student, Kurt Alder, [4] in properly identifying the products (4 and 6, Scheme 1) arising from the reaction of cyclopentadiene (1) with quinone (2) denotes a historic event in the field of chemistry for which these two individuals were rewarded with a reaction that would henceforth bear their names. [5] With prophetic foresight, Diels and Alder clearly anticipated the importance of this discovery in their landmark 1928 paper, particularly as applied to natural product synthesis, through the following remark: ™Thus it appears to us that the possibility of synthesis of complex compounds related to or identical with natural products such as terpenes, sesquiterpenes, perhaps even alkaloids, has been moved to the near prospect.∫ However, in an intriguing moment of scientific territoriality, which might appear slightly off-color or even amusing to a contem-Scheme 1. The discovery of the Diels ± Alder reaction in 1928, a reaction for which the namesakes would receive the Nobel Prize in Chemistry in 1950: Diels the professor, Alder the student.

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Total Synthesis of (±)‐Lysergic Acid by an Intramolecular Imino‐Diels‐Alder Reaction. Preliminary communication

Cited by 94 publications

References 29 publications

The Diels-Alder Reaction in Total Synthesis

The Diels-Alder Reaction in Total Synthesis

Die Diels-Alder-Reaktion in der Totalsynthese

Professor K. C. Nicolaou*Department of Chemistry, The Scripps Research Institute and the University of California, San Diego, 10550 North Torrey Pines Road, La Jolla, California 92037 USA.

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