Prostaglandins, thromboxanes, leukotrienes, and related arachidonic acid metabolites

Hart, Terance W.

doi:10.1039/np9880500001

Cited by 10 publications

(1 citation statement)

References 39 publications

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“…The allylic alcohol motif is widespread in natural compounds − or in biologically relevant molecules . Its construction has received intensive attention, because allylic alcohols are versatile precursors of various functionalities and moieties in organic synthesis. − Furthermore, they are exploited in the preparation of pharmaceuticals, fragrances, and agrochemicals. , Therefore, many efforts have been dedicated to their reactivity: metal-catalyzed allylic substitutions, − isomerizations, reductive couplings, radical allylations, , for instance.…”

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confidence: 99%

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji–Trost-Like “Palladium–Iodide” Catalyzed Coupling

Parisotto

Deagostino

2018

Org. Lett.

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An unprecedented efficient palladium(0)-catalyzed reaction of vinyl oxiranes with N-tosylhydrazones, affording "skipped" allylic alcohols in total regioselectivity and stereoselectivity, with excellent functional-group compatibility, is reported. In this Tsuji−Trost-like allylation, we propose the use of N-tosylhydrazones as a synthetic equivalent of α-styryl anions. More than 20 new products are described, including naturally occurring derivatives. A catalytic system involving an iodide (I − ) source is necessary to sustain the catalytic cycle.

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confidence: 99%

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji–Trost-Like “Palladium–Iodide” Catalyzed Coupling

Parisotto

Deagostino

2018

Org. Lett.

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Prostaglandins

Buchmann¹,

Rehwinkel²

2000

Ullmann's Encyclopedia of Industrial Chemistry

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Prostaglandins

Buchmann

Rehwinkel

2007

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. History 2. Structure, Nomenclature, and Physical Properties 3. Occurrence and Biosynthesis 4. Pharmacological Effects and Uses 5. Syntheses Prostaglandins are formed from arachidonic acid . Those and all other derivatives of arachidonic acid, e.g., prostacyclins, thromboxanes, leukotrienes, and lipoxines are called eicosanoids. Most eicosanoids are chemically and metabolically unstable. Therefore, many pharmaceutical companies have tried to improve the stability by modifying the original structures. Several of these analogues have already reached the market in different therapeutic indications or show promising results in clinical trials. This article describes the chemical and pharmacological properties of the natural derivatives and their analogues as well as the synthetic access to some of the natural compounds.

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Prostaglandins, thromboxanes, leukotrienes, and related arachidonic acid metabolites

Cited by 10 publications

References 39 publications

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji–Trost-Like “Palladium–Iodide” Catalyzed Coupling

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji–Trost-Like “Palladium–Iodide” Catalyzed Coupling

Prostaglandins

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