Concise and Practical Total Synthesis of (+)-Abscisic Acid

[Image: see text] (+)-Abscisic acid 1 was obtained in a concise total synthesis from ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate (2) with 41% overall yield in seven steps. A hydroxyl group was stereoselectively introduced by Sharpless asymmetric epoxidation; then, the side chain was appe...

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Autores principales: Kim, Dahye, Koo, Sangho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7288699/
https://www.ncbi.nlm.nih.gov/pubmed/32548516
http://dx.doi.org/10.1021/acsomega.0c01332
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author Kim, Dahye
Koo, Sangho
author_facet Kim, Dahye
Koo, Sangho
author_sort Kim, Dahye
collection PubMed
description [Image: see text] (+)-Abscisic acid 1 was obtained in a concise total synthesis from ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate (2) with 41% overall yield in seven steps. A hydroxyl group was stereoselectively introduced by Sharpless asymmetric epoxidation; then, the side chain was appended with dimethyl 2-(propan-2-ylidene)malonate (7); subsequently, selective decarboxylation of diacid 8 established the Z-configuration of the conjugated acid 1.
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spelling pubmed-72886992020-06-15 Concise and Practical Total Synthesis of (+)-Abscisic Acid Kim, Dahye Koo, Sangho ACS Omega [Image: see text] (+)-Abscisic acid 1 was obtained in a concise total synthesis from ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate (2) with 41% overall yield in seven steps. A hydroxyl group was stereoselectively introduced by Sharpless asymmetric epoxidation; then, the side chain was appended with dimethyl 2-(propan-2-ylidene)malonate (7); subsequently, selective decarboxylation of diacid 8 established the Z-configuration of the conjugated acid 1. American Chemical Society 2020-05-29 /pmc/articles/PMC7288699/ /pubmed/32548516 http://dx.doi.org/10.1021/acsomega.0c01332 Text en Copyright © 2020 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
Koo, Sangho
Concise and Practical Total Synthesis of (+)-Abscisic Acid
title Concise and Practical Total Synthesis of (+)-Abscisic Acid
title_full Concise and Practical Total Synthesis of (+)-Abscisic Acid
title_fullStr Concise and Practical Total Synthesis of (+)-Abscisic Acid
title_full_unstemmed Concise and Practical Total Synthesis of (+)-Abscisic Acid
title_short Concise and Practical Total Synthesis of (+)-Abscisic Acid
title_sort concise and practical total synthesis of (+)-abscisic acid
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7288699/
https://www.ncbi.nlm.nih.gov/pubmed/32548516
http://dx.doi.org/10.1021/acsomega.0c01332
work_keys_str_mv AT kimdahye conciseandpracticaltotalsynthesisofabscisicacid
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