Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

Ramon Alibés; Pilar Blanco; Eva Casas; Montserrat Closa; Pedro De March; Marta Figueredo; Josep Font; Elena Sanfeliu; Ángel Álvarez-Larena

doi:10.1021/jo047867q

Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

Ramon Alibés, Pilar Blanco, Eva Casas, Montserrat Closa, Pedro De March, Marta Figueredo, Josep Font, Elena Sanfeliu, Ángel Álvarez-Larena

Departament de Química

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(Chemical Equation Presented) A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids. © 2005 American Chemical Society.

Idioma original	Anglès
Pàgines (de-a)	3157-3167
Revista	Journal of Organic Chemistry
Volum	70
Número	8
DOIs	https://doi.org/10.1021/jo047867q
Estat de la publicació	Publicada - 15 d’abr. 2005

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10.1021/jo047867q

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@article{8c06ac33bc88481c96ba63180008cc97,

title = "Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids",

abstract = "(Chemical Equation Presented) A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids. {\textcopyright} 2005 American Chemical Society.",

author = "Ramon Alib{\'e}s and Pilar Blanco and Eva Casas and Montserrat Closa and {De March}, Pedro and Marta Figueredo and Josep Font and Elena Sanfeliu and {\'A}ngel {\'A}lvarez-Larena",

year = "2005",

month = apr,

day = "15",

doi = "10.1021/jo047867q",

language = "English",

volume = "70",

pages = "3157--3167",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

AU - Alibés, Ramon

AU - Blanco, Pilar

AU - Casas, Eva

AU - Closa, Montserrat

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Sanfeliu, Elena

AU - Álvarez-Larena, Ángel

PY - 2005/4/15

Y1 - 2005/4/15

N2 - (Chemical Equation Presented) A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids. © 2005 American Chemical Society.

AB - (Chemical Equation Presented) A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C6 olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids. © 2005 American Chemical Society.

U2 - 10.1021/jo047867q

DO - 10.1021/jo047867q

M3 - Article

SN - 0022-3263

VL - 70

SP - 3157

EP - 3167

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

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