Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A

We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck a...

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Detalles Bibliográficos
Autores principales: Zhang, Tingrong, Miao, Shaojie, Zhang, Mingxiao, Liu, Wenjie, Wang, Liang, Chen, Yue
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8066987/
https://www.ncbi.nlm.nih.gov/pubmed/33807472
http://dx.doi.org/10.3390/md19040198
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author Zhang, Tingrong
Miao, Shaojie
Zhang, Mingxiao
Liu, Wenjie
Wang, Liang
Chen, Yue
author_facet Zhang, Tingrong
Miao, Shaojie
Zhang, Mingxiao
Liu, Wenjie
Wang, Liang
Chen, Yue
author_sort Zhang, Tingrong
collection PubMed
description We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck asymmetric vinylogous aldol reaction was employed to improve this transformation.
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spelling pubmed-80669872021-04-25 Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A Zhang, Tingrong Miao, Shaojie Zhang, Mingxiao Liu, Wenjie Wang, Liang Chen, Yue Mar Drugs Communication We have accomplished a 10-step (longest linear) total synthesis of nannocystin A on a four hundred milligram scale. The previously reported Kobayashi vinylogous Mukaiyama aldol reaction to connect C4 and C5 was unreproducible during the scaling up process. A more convenient and cost-efficient Keck asymmetric vinylogous aldol reaction was employed to improve this transformation. MDPI 2021-03-31 /pmc/articles/PMC8066987/ /pubmed/33807472 http://dx.doi.org/10.3390/md19040198 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Zhang, Tingrong
Miao, Shaojie
Zhang, Mingxiao
Liu, Wenjie
Wang, Liang
Chen, Yue
Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A
title Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A
title_full Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A
title_fullStr Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A
title_full_unstemmed Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A
title_short Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A
title_sort optimization of two steps in scale-up synthesis of nannocystin a
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8066987/
https://www.ncbi.nlm.nih.gov/pubmed/33807472
http://dx.doi.org/10.3390/md19040198
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AT liuwenjie optimizationoftwostepsinscaleupsynthesisofnannocystina
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