Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone

[Image: see text] A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (−)-Geissman–Waiss lactone starting from meso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the r...

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Autores principales: Ali, Mohd Tajudin Mohd, Husin, Zurhana Mat, Macabeo, Allan Patrick G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8482504/
https://www.ncbi.nlm.nih.gov/pubmed/34604643
http://dx.doi.org/10.1021/acsomega.1c03251
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author Ali, Mohd Tajudin Mohd
Husin, Zurhana Mat
Macabeo, Allan Patrick G.
author_facet Ali, Mohd Tajudin Mohd
Husin, Zurhana Mat
Macabeo, Allan Patrick G.
author_sort Ali, Mohd Tajudin Mohd
collection PubMed
description [Image: see text] A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (−)-Geissman–Waiss lactone starting from meso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5S stereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids.
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spelling pubmed-84825042021-10-01 Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone Ali, Mohd Tajudin Mohd Husin, Zurhana Mat Macabeo, Allan Patrick G. ACS Omega [Image: see text] A short, asymmetric synthesis of tetrahydro-2H-furo[3,2-b]pyrrole derivatives and (−)-Geissman–Waiss lactone starting from meso-cyclohexadiene epoxide is described. Pivotal transformations in the developed synthetic procedure include asymmetric epoxide ring opening to install the requisite 1S,5S stereocenters and oxidative lactonization/lactamization sequences. This route provides a streamlined synthetic pathway toward necine alkaloids. American Chemical Society 2021-09-15 /pmc/articles/PMC8482504/ /pubmed/34604643 http://dx.doi.org/10.1021/acsomega.1c03251 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Ali, Mohd Tajudin Mohd
Husin, Zurhana Mat
Macabeo, Allan Patrick G.
Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone
title Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone
title_full Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone
title_fullStr Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone
title_full_unstemmed Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone
title_short Asymmetric Synthesis of N,O-Heterobicyclic Octanes and (−)-Geissman–Waiss Lactone
title_sort asymmetric synthesis of n,o-heterobicyclic octanes and (−)-geissman–waiss lactone
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8482504/
https://www.ncbi.nlm.nih.gov/pubmed/34604643
http://dx.doi.org/10.1021/acsomega.1c03251
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