11-Step Total Synthesis of (−)-Maoecrystal V

[Image: see text] An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of wh...

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Autores principales: Cernijenko, Artiom, Risgaard, Rune, Baran, Phil S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4974602/
https://www.ncbi.nlm.nih.gov/pubmed/27457680
http://dx.doi.org/10.1021/jacs.6b06623
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author Cernijenko, Artiom
Risgaard, Rune
Baran, Phil S.
author_facet Cernijenko, Artiom
Risgaard, Rune
Baran, Phil S.
author_sort Cernijenko, Artiom
collection PubMed
description [Image: see text] An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (−)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.
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spelling pubmed-49746022016-08-08 11-Step Total Synthesis of (−)-Maoecrystal V Cernijenko, Artiom Risgaard, Rune Baran, Phil S. J Am Chem Soc [Image: see text] An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (−)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product. American Chemical Society 2016-07-26 2016-08-03 /pmc/articles/PMC4974602/ /pubmed/27457680 http://dx.doi.org/10.1021/jacs.6b06623 Text en Copyright © 2016 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 Cernijenko, Artiom
Risgaard, Rune
Baran, Phil S.
11-Step Total Synthesis of (−)-Maoecrystal V
title 11-Step Total Synthesis of (−)-Maoecrystal V
title_full 11-Step Total Synthesis of (−)-Maoecrystal V
title_fullStr 11-Step Total Synthesis of (−)-Maoecrystal V
title_full_unstemmed 11-Step Total Synthesis of (−)-Maoecrystal V
title_short 11-Step Total Synthesis of (−)-Maoecrystal V
title_sort 11-step total synthesis of (−)-maoecrystal v
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4974602/
https://www.ncbi.nlm.nih.gov/pubmed/27457680
http://dx.doi.org/10.1021/jacs.6b06623
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