Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids

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Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids. / Gromova, M. A.; Kharitonov, Yu V.; Rybalova, T. V. et al.

In: Chemistry of Natural Compounds, Vol. 55, No. 5, 01.09.2019, p. 871-877.

Research output: Contribution to journal › Article › peer-review

Harvard

Gromova, MA, Kharitonov, YV, Rybalova, TV & Shul’ts, EE 2019, 'Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids', Chemistry of Natural Compounds, vol. 55, no. 5, pp. 871-877. https://doi.org/10.1007/s10600-019-02836-y

APA

Gromova, M. A., Kharitonov, Y. V., Rybalova, T. V., & Shul’ts, E. E. (2019). Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids. Chemistry of Natural Compounds, 55(5), 871-877. https://doi.org/10.1007/s10600-019-02836-y

Vancouver

Gromova MA, Kharitonov YV, Rybalova TV, Shul’ts EE. Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids. Chemistry of Natural Compounds. 2019 Sept 1;55(5):871-877. doi: 10.1007/s10600-019-02836-y

Author

Gromova, M. A. ; Kharitonov, Yu V. ; Rybalova, T. V. et al. / Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids. In: Chemistry of Natural Compounds. 2019 ; Vol. 55, No. 5. pp. 871-877.

BibTeX

@article{22bd2bd2560c41c2b615039ea13a2c2a,

title = "Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids",

abstract = "The synthesis and properties of tricyclic pimaranes containing a C-16 β-carboline are reported. A Pictet–Spengler reaction of methyl 15-oxo-16-formylisopimarate (prepared in situ from the 15-oxo-15,16-dihydroisopimarate) and tryptamine or tryptophan methyl ester in the presence of trifluoroacetic acid formed a mixture of terpenoid 1,2,3,4-tetrahydro-β-carbolines, 3,4-dihydro-β-carbolines, and β-carbolines. Tetrahydro- and dihydro-β-carbolines in CHCl3 were oxidized to the corresponding β-carbolines by treatment in air with basic Al2O3.",

keywords = "diterpenoids, heterocyclic compounds, isopimaric acid, Pictet–Spengler reaction, XSA, β-carbolines, beta-carbolines, DESIGN, Pictet-Spengler reaction, DERIVATIVES, MOLECULES",

author = "Gromova, {M. A.} and Kharitonov, {Yu V.} and Rybalova, {T. V.} and Shul{\textquoteright}ts, {E. E.}",

year = "2019",

month = sep,

day = "1",

doi = "10.1007/s10600-019-02836-y",

language = "English",

volume = "55",

pages = "871--877",

journal = "Chemistry of Natural Compounds",

issn = "0009-3130",

publisher = "Springer New York",

number = "5",

}

RIS

TY - JOUR

T1 - Synthetic Transformations of Higher Terpenoids. 38.* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids

AU - Gromova, M. A.

AU - Kharitonov, Yu V.

AU - Rybalova, T. V.

AU - Shul’ts, E. E.

PY - 2019/9/1

Y1 - 2019/9/1

N2 - The synthesis and properties of tricyclic pimaranes containing a C-16 β-carboline are reported. A Pictet–Spengler reaction of methyl 15-oxo-16-formylisopimarate (prepared in situ from the 15-oxo-15,16-dihydroisopimarate) and tryptamine or tryptophan methyl ester in the presence of trifluoroacetic acid formed a mixture of terpenoid 1,2,3,4-tetrahydro-β-carbolines, 3,4-dihydro-β-carbolines, and β-carbolines. Tetrahydro- and dihydro-β-carbolines in CHCl3 were oxidized to the corresponding β-carbolines by treatment in air with basic Al2O3.

AB - The synthesis and properties of tricyclic pimaranes containing a C-16 β-carboline are reported. A Pictet–Spengler reaction of methyl 15-oxo-16-formylisopimarate (prepared in situ from the 15-oxo-15,16-dihydroisopimarate) and tryptamine or tryptophan methyl ester in the presence of trifluoroacetic acid formed a mixture of terpenoid 1,2,3,4-tetrahydro-β-carbolines, 3,4-dihydro-β-carbolines, and β-carbolines. Tetrahydro- and dihydro-β-carbolines in CHCl3 were oxidized to the corresponding β-carbolines by treatment in air with basic Al2O3.

KW - diterpenoids

KW - heterocyclic compounds

KW - isopimaric acid

KW - Pictet–Spengler reaction

KW - XSA

KW - β-carbolines

KW - beta-carbolines

KW - DESIGN

KW - Pictet-Spengler reaction

KW - DERIVATIVES

KW - MOLECULES

UR - http://www.scopus.com/inward/record.url?scp=85074480854&partnerID=8YFLogxK

U2 - 10.1007/s10600-019-02836-y

DO - 10.1007/s10600-019-02836-y

M3 - Article

AN - SCOPUS:85074480854

VL - 55

SP - 871

EP - 877

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 5

ER -

ID: 22364464