Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks. / Franzyk, Henrik; Frederiksen, S M; Jensen, S R.

In: Journal of Natural Products, Vol. 63, No. 5, 2000, p. 592-5.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Franzyk, H, Frederiksen, SM & Jensen, SR 2000, 'Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks', Journal of Natural Products, vol. 63, no. 5, pp. 592-5.

APA

Franzyk, H., Frederiksen, S. M., & Jensen, S. R. (2000). Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks. Journal of Natural Products, 63(5), 592-5.

Vancouver

Franzyk H, Frederiksen SM, Jensen SR. Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks. Journal of Natural Products. 2000;63(5):592-5.

Author

Franzyk, Henrik ; Frederiksen, S M ; Jensen, S R. / Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks. In: Journal of Natural Products. 2000 ; Vol. 63, No. 5. pp. 592-5.

Bibtex

@article{6f30939d6306457a9d608ef51b301160,
title = "Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks",
abstract = "The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.",
keywords = "Aza Compounds, Bicyclo Compounds, Glucosides, Hypoglycemic Agents, Indicators and Reagents, Iridoid Glucosides, Iridoids, Pyrans, Substance P",
author = "Henrik Franzyk and Frederiksen, {S M} and Jensen, {S R}",
year = "2000",
language = "English",
volume = "63",
pages = "592--5",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "5",

}

RIS

TY - JOUR

T1 - Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks

AU - Franzyk, Henrik

AU - Frederiksen, S M

AU - Jensen, S R

PY - 2000

Y1 - 2000

N2 - The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

AB - The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

KW - Aza Compounds

KW - Bicyclo Compounds

KW - Glucosides

KW - Hypoglycemic Agents

KW - Indicators and Reagents

KW - Iridoid Glucosides

KW - Iridoids

KW - Pyrans

KW - Substance P

M3 - Journal article

C2 - 10843565

VL - 63

SP - 592

EP - 595

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 5

ER -

ID: 43211704