Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4

Our synthesis of the CDE ring fragment of pectenotoxin-4 utilised two key steps to make the complex bicyclic ketal unit: (i) a rhodium-catalysed vinyl group 1,4-addition as the major C–C bond forming step; (ii) a stereoselective Sharpless Asymmetric Dihydroxylation (SAD) of the resulting 1,1-disubst...

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Autores principales: Richardson, Melodie S. W., Tame, Christopher J., Poole, Darren L., Donohoe, Timothy J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6601420/
https://www.ncbi.nlm.nih.gov/pubmed/31341588
http://dx.doi.org/10.1039/c9sc01761e
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author Richardson, Melodie S. W.
Tame, Christopher J.
Poole, Darren L.
Donohoe, Timothy J.
author_facet Richardson, Melodie S. W.
Tame, Christopher J.
Poole, Darren L.
Donohoe, Timothy J.
author_sort Richardson, Melodie S. W.
collection PubMed
description Our synthesis of the CDE ring fragment of pectenotoxin-4 utilised two key steps to make the complex bicyclic ketal unit: (i) a rhodium-catalysed vinyl group 1,4-addition as the major C–C bond forming step; (ii) a stereoselective Sharpless Asymmetric Dihydroxylation (SAD) of the resulting 1,1-disubstituted homoallylic alcohol. Subsequent acid-catalysed cyclisation afforded the desired [5,6]-bicyclic ketal of the target molecule. This methodology was shown to be compatible with the desired E ring fragment 35 in order to construct the CDE fragment 37 of pectenotoxin-4.
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spelling pubmed-66014202019-07-24 Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4 Richardson, Melodie S. W. Tame, Christopher J. Poole, Darren L. Donohoe, Timothy J. Chem Sci Chemistry Our synthesis of the CDE ring fragment of pectenotoxin-4 utilised two key steps to make the complex bicyclic ketal unit: (i) a rhodium-catalysed vinyl group 1,4-addition as the major C–C bond forming step; (ii) a stereoselective Sharpless Asymmetric Dihydroxylation (SAD) of the resulting 1,1-disubstituted homoallylic alcohol. Subsequent acid-catalysed cyclisation afforded the desired [5,6]-bicyclic ketal of the target molecule. This methodology was shown to be compatible with the desired E ring fragment 35 in order to construct the CDE fragment 37 of pectenotoxin-4. Royal Society of Chemistry 2019-05-24 /pmc/articles/PMC6601420/ /pubmed/31341588 http://dx.doi.org/10.1039/c9sc01761e Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Richardson, Melodie S. W.
Tame, Christopher J.
Poole, Darren L.
Donohoe, Timothy J.
Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
title Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
title_full Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
title_fullStr Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
title_full_unstemmed Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
title_short Rhodium-catalysed vinyl 1,4-conjugate addition coupled with Sharpless asymmetric dihydroxylation in the synthesis of the CDE ring fragment of pectenotoxin-4
title_sort rhodium-catalysed vinyl 1,4-conjugate addition coupled with sharpless asymmetric dihydroxylation in the synthesis of the cde ring fragment of pectenotoxin-4
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6601420/
https://www.ncbi.nlm.nih.gov/pubmed/31341588
http://dx.doi.org/10.1039/c9sc01761e
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