The domino chemistry approach to molecular complexity: high-yielding bis-hetero intramolecular Diels–Alder reactions with ketone components

Chanu, Angeline; Castellote, Isabel; Commeureuc, Aurélien G. J.; Safir, Imad; Arseniyadis, Stellios

doi:10.1016/j.tetasy.2006.09.003

Cited by 13 publications

(2 citation statements)

References 38 publications

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“…Subsequent ring contraction of 174 with potassium hydroxide followed by methylation gave cyclopentane 175. In the synthesis of 1-epi-pathylactone A (176), 133 oxidative cleavage of diol 177 followed by a bis-hetero-Diels-Alder reaction gave 179. Upon ozonolysis, the methoxyfuran 180 was formed and converted into the natural product.…”

Section: Ring-expansion and -Contraction Reactionsmentioning

confidence: 99%

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

Bradshaw¹,

Bonjoch²

2011

Synlett

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The Hajos-Parrish-Eder-Sauer-Wiechert reaction can be considered as the origin of asymmetric organocatalysis, giving rise to the Wieland-Miescher ketone 1 (WMK), a versatile building block. Although 40 years have passed since its discovery, a highly enantioselective and scalable synthesis of the WMK has remained elusive. This account details a solution to that problem that came about in the development of methodology towards C-8a WMK analogues as part of the total synthesis of complex diterpene natural products. The work has been placed in the context of the historical background and reactivity of this important building block, highlighting the challenges faced by organocatalysis in large-scale reactions.

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Section: Ring-expansion and -Contraction Reactionsmentioning

confidence: 99%

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

Bradshaw¹,

Bonjoch²

2011

Synlett

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“…2–5 h, TLC monitoring) 15. With ever‐growing environmental concern, we later developed a green protocol16 using PhI(OAc) 2 as the oxidant,17 which shows a reactivity pattern similar to that of Pb(OAc) 4 . Under these conditions (Scheme ) the oxidative pericyclic domino reaction allowed for easy access of the target A‐norsteroid 6 on large scale and in high isolated yields as an epimeric mixture ( 6b / 6a = 4:1, 90 % combined yield).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Norsesquiterpene Spirolactone/Steroidal Hybrid by Using an Environmentally Friendly Domino Reaction as a Key Step

et al. 2007

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2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

Duschek

Kirsch

2011

Angewandte Chemie

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Seit seiner Entdeckung durch Christoph Hartmann und Victor Meyer im Jahr 1893 hat sich 2‐Iodoxybenzoesäure (IBX) zu einem geradezu ubiquitär einsetzbaren Oxidationsmittel entwickelt. Insbesondere in den vergangenen zehn Jahren wurde eine Vielzahl von Anwendungsmöglichkeiten beschrieben, die weit über die einfache Oxidation von Alkoholen hinausgehen. Dieser Aufsatz behandelt das Potenzial von IBX in der Synthese, wobei insbesondere unerwartete Reaktivitäten und moderne Anwendungen im Mittelpunkt der Diskussion stehen.

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The domino chemistry approach to molecular complexity: high-yielding bis-hetero intramolecular Diels–Alder reactions with ketone components

Cited by 13 publications

References 38 publications

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

The Wieland-Miescher Ketone: A Journey from Organocatalysis to Natural Product Synthesis

Synthesis of a Norsesquiterpene Spirolactone/Steroidal Hybrid by Using an Environmentally Friendly Domino Reaction as a Key Step

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

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