Preparation of intermediates for the synthesis of polycyclic alkaloids: A new access to the azabicyclic core of the Stemona alkaloids

Pau Cid; Montserrat Closa; Pedro De March; Marta Figueredo; Josep Font; Elena Sanfeliu; Angeles Soria

doi:10.1002/ejoc.200400322

Preparation of intermediates for the synthesis of polycyclic alkaloids: A new access to the azabicyclic core of the Stemona alkaloids

Pau Cid, Montserrat Closa, Pedro De March, Marta Figueredo, Josep Font, Elena Sanfeliu, Angeles Soria

Department of Chemistry

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

18 Citations (Scopus)

Abstract

Several isoxazolidines, derived from the 1,3-dipolar cycloaddition of α,β-hexenolides to cyclic nitrones, were converted into the corresponding piperidine- and pyrrolidine-oxepinones by reduction of the nitrogen-oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1-azabicyclo[5.3.0]decane core of the Sfemona alkaloids. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Original language	English
Pages (from-to)	4215-4233
Journal	European Journal of Organic Chemistry
Issue number	20
DOIs	https://doi.org/10.1002/ejoc.200400322
Publication status	Published - 11 Oct 2004

Keywords

Isoxazolidine
Oxepinone
Piperidine
Polycyclic alkaloids
Pyrrolidine
Stemona

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title = "Preparation of intermediates for the synthesis of polycyclic alkaloids: A new access to the azabicyclic core of the Stemona alkaloids",

abstract = "Several isoxazolidines, derived from the 1,3-dipolar cycloaddition of α,β-hexenolides to cyclic nitrones, were converted into the corresponding piperidine- and pyrrolidine-oxepinones by reduction of the nitrogen-oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1-azabicyclo[5.3.0]decane core of the Sfemona alkaloids. {\textcopyright} Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.",

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author = "Pau Cid and Montserrat Closa and {De March}, Pedro and Marta Figueredo and Josep Font and Elena Sanfeliu and Angeles Soria",

year = "2004",

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doi = "10.1002/ejoc.200400322",

language = "English",

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Preparation of intermediates for the synthesis of polycyclic alkaloids: A new access to the azabicyclic core of the Stemona alkaloids. / Cid, Pau; Closa, Montserrat; De March, Pedro; Figueredo, Marta; Font, Josep; Sanfeliu, Elena; Soria, Angeles.

In: European Journal of Organic Chemistry, No. 20, 11.10.2004, p. 4215-4233.

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

TY - JOUR

T1 - Preparation of intermediates for the synthesis of polycyclic alkaloids: A new access to the azabicyclic core of the Stemona alkaloids

AU - Cid, Pau

AU - Closa, Montserrat

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Sanfeliu, Elena

AU - Soria, Angeles

PY - 2004/10/11

Y1 - 2004/10/11

N2 - Several isoxazolidines, derived from the 1,3-dipolar cycloaddition of α,β-hexenolides to cyclic nitrones, were converted into the corresponding piperidine- and pyrrolidine-oxepinones by reduction of the nitrogen-oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1-azabicyclo[5.3.0]decane core of the Sfemona alkaloids. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

AB - Several isoxazolidines, derived from the 1,3-dipolar cycloaddition of α,β-hexenolides to cyclic nitrones, were converted into the corresponding piperidine- and pyrrolidine-oxepinones by reduction of the nitrogen-oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1-azabicyclo[5.3.0]decane core of the Sfemona alkaloids. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

KW - Isoxazolidine

KW - Oxepinone

KW - Piperidine

KW - Polycyclic alkaloids

KW - Pyrrolidine

KW - Stemona

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DO - 10.1002/ejoc.200400322

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EP - 4233

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