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

Department of Chemistry

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

11 Citations (Scopus)

Abstract

© 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.

Original language	English
Pages (from-to)	5052-5057
Journal	Journal of Organic Chemistry
Volume	83
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.8b00390
Publication status	Published - 4 May 2018

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10.1021/acs.joc.8b00390

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

CCDC 1554877: Experimental Crystal Structure Determination
Alujas-Burgos, S. (Creator), Oliveras-González, C. (Creator), Álvarez-Larena, Á. (Creator), Bayón, P. (Creator) & Figueredo, M. (Creator), 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

Cite this

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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,

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

language = "English",

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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

Abstract

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CCDC 1554877: Experimental Crystal Structure Determination

Cite this