Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses

[Image: see text] A new olefination protocol utilizing ethyl bromoacetate was highlighted, in which magnesium enolate of the ester coupled with C(20) dialdehyde 6, and double eliminations of the protected hydroxyl groups and bromine atoms of the coupling bromohydrin product, efficiently produced nor...

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Autores principales: Kim, Dahye, Alam, Mohammad Shariful, Chung, Wook-Jin, Koo, Sangho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648602/
https://www.ncbi.nlm.nih.gov/pubmed/31460094
http://dx.doi.org/10.1021/acsomega.9b00900
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author Kim, Dahye
Alam, Mohammad Shariful
Chung, Wook-Jin
Koo, Sangho
author_facet Kim, Dahye
Alam, Mohammad Shariful
Chung, Wook-Jin
Koo, Sangho
author_sort Kim, Dahye
collection PubMed
description [Image: see text] A new olefination protocol utilizing ethyl bromoacetate was highlighted, in which magnesium enolate of the ester coupled with C(20) dialdehyde 6, and double eliminations of the protected hydroxyl groups and bromine atoms of the coupling bromohydrin product, efficiently produced norbixin 1 after concomitant hydrolysis of the ester. A new (C(7) + C(10) + C(7)) disconnection approach was demonstrated for the synthesis of norbixin ethyl ester 2 by the Julia–Kocienski olefination of novel C(7) benzothiazolyl-sulfone 11 and C(10) 2,7-dimethyl-2,4,6-octatrienedial (12).
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spelling pubmed-66486022019-08-27 Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses Kim, Dahye Alam, Mohammad Shariful Chung, Wook-Jin Koo, Sangho ACS Omega [Image: see text] A new olefination protocol utilizing ethyl bromoacetate was highlighted, in which magnesium enolate of the ester coupled with C(20) dialdehyde 6, and double eliminations of the protected hydroxyl groups and bromine atoms of the coupling bromohydrin product, efficiently produced norbixin 1 after concomitant hydrolysis of the ester. A new (C(7) + C(10) + C(7)) disconnection approach was demonstrated for the synthesis of norbixin ethyl ester 2 by the Julia–Kocienski olefination of novel C(7) benzothiazolyl-sulfone 11 and C(10) 2,7-dimethyl-2,4,6-octatrienedial (12). American Chemical Society 2019-06-07 /pmc/articles/PMC6648602/ /pubmed/31460094 http://dx.doi.org/10.1021/acsomega.9b00900 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kim, Dahye
Alam, Mohammad Shariful
Chung, Wook-Jin
Koo, Sangho
Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses
title Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses
title_full Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses
title_fullStr Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses
title_full_unstemmed Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses
title_short Bromoacetate Olefination Protocol for Norbixin and Julia–Kocienski Olefination for Its Ester Syntheses
title_sort bromoacetate olefination protocol for norbixin and julia–kocienski olefination for its ester syntheses
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648602/
https://www.ncbi.nlm.nih.gov/pubmed/31460094
http://dx.doi.org/10.1021/acsomega.9b00900
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