Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine

Sílvia Alujas-Burgos; Cristina Oliveras-González; Ángel Álvarez-Larena; Pau Bayón; Marta Figueredo

doi:10.1021/acs.joc.8b00390

Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine

Sílvia Alujas-Burgos, Cristina Oliveras-González, Ángel Álvarez-Larena, Pau Bayón, Marta Figueredo

Departamento de Química

Producción científica: Contribución a una revista › Artículo › Investigación › revisión exhaustiva

11 Citas (Scopus)

Resumen

© 2018 American Chemical Society. A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a-epi-hippocasine.

Idioma original	Inglés
Páginas (desde-hasta)	5052-5057
Publicación	Journal of Organic Chemistry
Volumen	83
N.º	9
DOI	https://doi.org/10.1021/acs.joc.8b00390
Estado	Publicada - 4 may 2018

Acceder al documento

10.1021/acs.joc.8b00390

https://ddd.uab.cat/record/189631

CCDC 1554877: Experimental Crystal Structure Determination
Alujas-Burgos, S. (Creador), Oliveras-González, C. (Creador), Álvarez-Larena, Á. (Creador), Bayón, P. (Creador) & Figueredo, M. (Creador), Cambridge Crystallographic Data Centre, 8 jun 2017
DOI: 10.5517/ccdc.csd.cc1p5zb5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1p5zb5&sid=DataCite
Dataset: Conjunto de datos

Citar esto

@article{2da5eed925a84119ba5895ef73d1e37a,

title = "Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine",

abstract = "{\textcopyright} 2018 American Chemical Society. A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a-epi-hippocasine.",

author = "S{\'i}lvia Alujas-Burgos and Cristina Oliveras-Gonz{\'a}lez and {\'A}ngel {\'A}lvarez-Larena and Pau Bay{\'o}n and Marta Figueredo",

year = "2018",

month = may,

day = "4",

doi = "10.1021/acs.joc.8b00390",

language = "English",

volume = "83",

pages = "5052--5057",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine. / Alujas-Burgos, Sílvia; Oliveras-González, Cristina; Álvarez-Larena, Ángel et al.
En: Journal of Organic Chemistry, Vol. 83, N.º 9, 04.05.2018, p. 5052-5057.

Producción científica: Contribución a una revista › Artículo › Investigación › revisión exhaustiva

TY - JOUR

T1 - Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine

AU - Alujas-Burgos, Sílvia

AU - Oliveras-González, Cristina

AU - Álvarez-Larena, Ángel

AU - Bayón, Pau

AU - Figueredo, Marta

PY - 2018/5/4

Y1 - 2018/5/4

N2 - © 2018 American Chemical Society. A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a-epi-hippocasine.

AB - © 2018 American Chemical Society. A new strategy for the stereoselective synthesis of alkaloids with perhydro-9b-azaphenalene skeleton has been developed. The starting material is the substituted glutarimide derivative 1, readily available in either enantiomeric form through the palladium-catalyzed asymmetric allylic alkylation of glutarimide. The strategy relies on an iterative methodology encompassing two nucleophilic allylations and two ring closing metathesis processes. The approach has been used in the first synthesis of (-)-9a-epi-hippocasine.

U2 - 10.1021/acs.joc.8b00390

DO - 10.1021/acs.joc.8b00390

M3 - Article

SN - 0022-3263

VL - 83

SP - 5052

EP - 5057

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of (-)-9a epi-Hippocasine

Resumen

Acceder al documento

Huella

Conjuntos de datos

CCDC 1554877: Experimental Crystal Structure Determination

Citar esto