Synthesis of an advanced intermediate of the jatrophane diterpene Pl-4: A dibromide coupling approach

R. Fürst; U. Rinner

doi:10.1021/jo401480t

Synthesis of an advanced intermediate of the jatrophane diterpene Pl-4: A dibromide coupling approach

Publikation: Beitrag in Fachzeitschrift › Artikel › Begutachtung

Abstract

The preparation of an advanced intermediate toward the synthesis of the jatrophane diterpene Pl-4 is described. The key step is a regioselective chelation-controlled lithiation of the (Z)-configured bromide in the corresponding vinyl dibromide precursor. The method outlined within this Article is suitable for the facile access of sterically hindered internal vinyl halides for further coupling reactions.

Originalsprache	Englisch
Seiten (von - bis)	8748-8758
Seitenumfang	11
Fachzeitschrift	J. Org. Chem.
Jahrgang	78
Ausgabenummer	17
DOIs	https://doi.org/10.1021/jo401480t
Publikationsstatus	Veröffentlicht - 6 Sep. 2013
Extern publiziert	Ja

Forschungsfelder

Gesamtsynthese
Natürliche Produkte
Terpene
Stereoselektive Synthese

IMC Forschungsschwerpunkte

Materials science

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

104015 Organische Chemie
104013 Naturstoffchemie

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10.1021/jo401480t

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title = "Synthesis of an advanced intermediate of the jatrophane diterpene Pl-4: A dibromide coupling approach",

abstract = "The preparation of an advanced intermediate toward the synthesis of the jatrophane diterpene Pl-4 is described. The key step is a regioselective chelation-controlled lithiation of the (Z)-configured bromide in the corresponding vinyl dibromide precursor. The method outlined within this Article is suitable for the facile access of sterically hindered internal vinyl halides for further coupling reactions.",

keywords = "Bromides, Diterpenes, Molecular Conformation, Stereoisomerism, Chemistry, Organic compounds, bromide, diterpene, halide, Pl 4 derivative, unclassified drug, Coupling reaction, Dibromide, Facile access, Lithiation, Regio-selective, Vinyl halides, alkylation, article, bromination, cross coupling reaction, drug structure, drug synthesis, proton nuclear magnetic resonance, Olefins, Bromides/chemistry, Diterpenes/chemical synthesis",

author = "R. F{\"u}rst and U. Rinner",

note = "Export Date: 13 June 2023; Cited By: 11; Correspondence Address: U. Rinner; Institute of Organic Chemistry, University of Vienna, 1090 Vienna, W{\"a}hringer Stra{\ss}e 38, Austria; email: [email protected]; CODEN: JOCEA",

year = "2013",

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day = "6",

doi = "10.1021/jo401480t",

language = "English",

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T2 - A dibromide coupling approach

AU - Fürst, R.

AU - Rinner, U.

N1 - Export Date: 13 June 2023; Cited By: 11; Correspondence Address: U. Rinner; Institute of Organic Chemistry, University of Vienna, 1090 Vienna, Währinger Straße 38, Austria; email: [email protected]; CODEN: JOCEA

PY - 2013/9/6

Y1 - 2013/9/6

N2 - The preparation of an advanced intermediate toward the synthesis of the jatrophane diterpene Pl-4 is described. The key step is a regioselective chelation-controlled lithiation of the (Z)-configured bromide in the corresponding vinyl dibromide precursor. The method outlined within this Article is suitable for the facile access of sterically hindered internal vinyl halides for further coupling reactions.

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KW - Bromides

KW - Diterpenes

KW - Molecular Conformation

KW - Stereoisomerism

KW - Chemistry

KW - Organic compounds

KW - bromide

KW - diterpene

KW - halide

KW - Pl 4 derivative

KW - unclassified drug

KW - Coupling reaction

KW - Dibromide

KW - Facile access

KW - Lithiation

KW - Regio-selective

KW - Vinyl halides

KW - alkylation

KW - article

KW - bromination

KW - cross coupling reaction

KW - drug structure

KW - drug synthesis

KW - proton nuclear magnetic resonance

KW - Olefins

KW - Bromides/chemistry

KW - Diterpenes/chemical synthesis

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JO - J. Org. Chem.

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ER -

Synthesis of an advanced intermediate of the jatrophane diterpene Pl-4: A dibromide coupling approach

Abstract

Forschungsfelder

IMC Forschungsschwerpunkte

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

Zugriff auf Dokument

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