Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D

[Image: see text] In this report, an expeditious synthesis of two new biologically active marine natural products serinolamide A and columbamide D is documented. This convergent approach involves the key steps such as hydrolytic kinetic resolution, cross metathesis, Grignard reaction, Johnson–Claise...

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Autores principales: Ghotekar, Ganesh S., Mujahid, Mohammad, Muthukrishnan, M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648212/
https://www.ncbi.nlm.nih.gov/pubmed/31459401
http://dx.doi.org/10.1021/acsomega.8b03417
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author Ghotekar, Ganesh S.
Mujahid, Mohammad
Muthukrishnan, M.
author_facet Ghotekar, Ganesh S.
Mujahid, Mohammad
Muthukrishnan, M.
author_sort Ghotekar, Ganesh S.
collection PubMed
description [Image: see text] In this report, an expeditious synthesis of two new biologically active marine natural products serinolamide A and columbamide D is documented. This convergent approach involves the key steps such as hydrolytic kinetic resolution, cross metathesis, Grignard reaction, Johnson–Claisen rearrangement, Mitsunobu, and so forth. Both of the target molecules were obtained from a common precursor (R)-7 with high enantioselectivity, less synthetic steps, and in good overall yields (serinolamide A 66% and columbamide D 62%).
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spelling pubmed-66482122019-08-27 Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D Ghotekar, Ganesh S. Mujahid, Mohammad Muthukrishnan, M. ACS Omega [Image: see text] In this report, an expeditious synthesis of two new biologically active marine natural products serinolamide A and columbamide D is documented. This convergent approach involves the key steps such as hydrolytic kinetic resolution, cross metathesis, Grignard reaction, Johnson–Claisen rearrangement, Mitsunobu, and so forth. Both of the target molecules were obtained from a common precursor (R)-7 with high enantioselectivity, less synthetic steps, and in good overall yields (serinolamide A 66% and columbamide D 62%). American Chemical Society 2019-01-15 /pmc/articles/PMC6648212/ /pubmed/31459401 http://dx.doi.org/10.1021/acsomega.8b03417 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 Ghotekar, Ganesh S.
Mujahid, Mohammad
Muthukrishnan, M.
Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D
title Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D
title_full Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D
title_fullStr Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D
title_full_unstemmed Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D
title_short Total Synthesis of Marine Natural Products Serinolamide A and Columbamide D
title_sort total synthesis of marine natural products serinolamide a and columbamide d
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648212/
https://www.ncbi.nlm.nih.gov/pubmed/31459401
http://dx.doi.org/10.1021/acsomega.8b03417
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