Carbonyl homologation with .alpha. substitution. A new synthesis of 4,4-disubstituted 2-cyclopentenones

Martin, Stephen F.; Chou, Ta Shue; PAYNE, C. W.

doi:10.1021/jo00434a043

Cited by 26 publications

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“…In this novel process for geminal acylation–alkylation, the first step corresponds to a carbonyl homologation reaction, whereas the second step involves the introduction of an electrophile at the carbon-atom α to the newly added aldehyde group. It occurred to us that the reaction of 134 with the phosphonate anion 136 would generate an enamine 137 that could be elaborated by reaction with an electrophile, followed by an aqueous acid workup to produce 135 . This procedure for effecting the geminal acylation–alkylation of ketone was successfully applied to a synthesis of O -methyljoubertiamine, , but not unexpectedly, the limitations of this approach for the synthesis of more complex alkaloids became quickly apparent because enamines react with only a limited number of reactive electrophiles.…”

Section: Synthesis Of Quaternary Carbon Atomsmentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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Diverse structural types of natural products and their mimics have served as targets of opportunity in our laboratory to inspire the discovery and development of new methods and strategies to assemble polyfunctional and polycyclic molecular architectures. Furthermore, our efforts toward identifying novel compounds having useful biological properties led to the creation of new targets, many of which posed synthetic challenges that required the invention of new methodology. In this Perspective, selected examples of how we have exploited a diverse range of natural products and their mimics to create, explore, and solve a variety of problems in chemistry and biology will be discussed. The journey was not without its twists and turns, but the unexpected often led to new revelations and insights. Indeed, in our recent excursion into applications of synthetic organic chemistry to neuroscience, avoiding the more-traveled paths was richly rewarding.

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Section: Synthesis Of Quaternary Carbon Atomsmentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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N-Morpholinomethyldiphenylphosphine Oxide

Fevig

2001

Encyclopedia of Reagents for Organic Synthesis

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Formation of Aldehydes and Ketones by Cyclization and Annulation Reactions

Larock

Dubrovskiy

Markina

2018

Comprehensive Organic Transformations

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Cyclization Spirocyclization and Spiroannulation One‐Carbon Annulation Two‐Carbon Annulation Three‐Carbon Annulation Four‐Carbon Annulation Five‐Carbon Annulation Five‐ and Six‐Carbon Annulation Six‐Carbon Annulation

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Carbonyl homologation with .alpha. substitution. A new synthesis of 4,4-disubstituted 2-cyclopentenones

Cited by 26 publications

References 1 publication

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Natural Products and Their Mimics as Targets of Opportunity for Discovery

N-Morpholinomethyldiphenylphosphine Oxide

Formation of Aldehydes and Ketones by Cyclization and Annulation Reactions

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