Alcaloides imidazoliques III (1) alcaloides du

Khuong-Huu, Françoise; Monseur, X.; G, Ratle; Lukacs, Gabor; Goutarel, R

doi:10.1016/s0040-4039(01)96047-2

Cited by 20 publications

(6 citation statements)

References 6 publications

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“…Hydrogenation [to give (9)], detosylation, and deprotection gave (lo), which was identical (t.1.c. and n.m.r., i.r., and mass spectra) with one component of an authentic sample of an inseparable mixture of isoprosopinine B and its side-chain ketone isomer isoprosopinine A (11). The synthesis therefore establishes unambiguously the structure of isoprosopinine B.…”

Section: ( 4 )mentioning

confidence: 72%

Total synthesis of (±)-isoprosopinine B and (±)-desoxoprosopinine

Holmes¹,

Thompson²,

Baxter³

et al. 1985

J. Chem. Soc., Chem. Commun.

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Section: ( 4 )mentioning

confidence: 72%

Total synthesis of (±)-isoprosopinine B and (±)-desoxoprosopinine

Holmes¹,

Thompson²,

Baxter³

et al. 1985

J. Chem. Soc., Chem. Commun.

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“…Isocynometrine is an imidazole alkaloid isolated from Cynometra species. It has been used in Africa as a traditional folk medicine with antitussive and analgesic activities . The structure of isocynometrine was determined by Riche et al as 7 , and Khuong-Huu et al reported its synthesis from 1-methyl-5-methoxycarbonylimidazole .…”

Section: Resultsmentioning

confidence: 99%

Palladium(II)-Catalyzed Synthesis of α-Alkylidene-γ-butyrolactams from N-Allylic 2-Alkynamides. Total Synthesis of (±)-Isocynodine and (±)-Isocynometrine

Xie

Liu

et al. 2001

J. Org. Chem.

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An efficient method for preparing alpha-alkylidene-gamma-butyrolactams via the Pd(II)-catalyzed cyclization of acyclic N-allylic 2-alkynamides via halopalladation, intramolecular olefin insertion, and beta-heteroatom elimination was developed. The reaction is less influenced by the leaving group and the concentration of the halide ions in comparison with the cyclization of acyclic alkynoates. The total syntheses of (+/-)-isocynodine and (+/-)-isocynometrine were realized using this method.

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“…γ-Butyrolactams (2-pyrrolidinones) are a class of versatile core structures found in many natural products (such as isocynometrine and Clausenamide) with interesting biological activities. They are also excellent precursors for the synthesis of biologically active pyrrolidine derivatives such as (+)-α-allokainic acid and its analogue (−)-α-kainic acid .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of γ-Butyrolactams by Photoinduced PhSe Group Transfer Radical Cyclization and Formal Synthesis of (±)-Isocynometrine with Diphenyldiselenide as Promoter

et al. 2009

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We have developed a strategy for constructing nitrogen heterocycles by photoinduced PhSe group transfer radical cyclization. trans-Alpha,beta-disubstituted gamma-butyrolactams (2-pyrrolidinones) were prepared in good yields (38-73%) with high regioselectivity and stereoselectivity from N-alkenyl alpha-PhSe beta-keto amides. Reaction outcomes were modulated by the steric effect of the substituents on the nitrogen atom of the cyclization precursors and the stereoelectronic effect of the substrates. Diphenyldiselenide, as an additive, was found to promote ring closure. The advantage of this strategy in natural product synthesis is demonstrated by a formal synthesis of (+/-)-isocynometrine.

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Alcaloides imidazoliques III (1) alcaloides du

Cited by 20 publications

References 6 publications

Total synthesis of (±)-isoprosopinine B and (±)-desoxoprosopinine

Total synthesis of (±)-isoprosopinine B and (±)-desoxoprosopinine

Palladium(II)-Catalyzed Synthesis of α-Alkylidene-γ-butyrolactams from N-Allylic 2-Alkynamides. Total Synthesis of (±)-Isocynodine and (±)-Isocynometrine

Synthesis of γ-Butyrolactams by Photoinduced PhSe Group Transfer Radical Cyclization and Formal Synthesis of (±)-Isocynometrine with Diphenyldiselenide as Promoter

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