11-Step Total Synthesis of Pallambins C and D

[Image: see text] The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a seq...

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Autores principales: Martinez, Luisruben P., Umemiya, Shigenobu, Wengryniuk, Sarah E., 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/PMC4919752/
https://www.ncbi.nlm.nih.gov/pubmed/27284962
http://dx.doi.org/10.1021/jacs.6b04816
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author Martinez, Luisruben P.
Umemiya, Shigenobu
Wengryniuk, Sarah E.
Baran, Phil S.
author_facet Martinez, Luisruben P.
Umemiya, Shigenobu
Wengryniuk, Sarah E.
Baran, Phil S.
author_sort Martinez, Luisruben P.
collection PubMed
description [Image: see text] The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.
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spelling pubmed-49197522016-06-27 11-Step Total Synthesis of Pallambins C and D Martinez, Luisruben P. Umemiya, Shigenobu Wengryniuk, Sarah E. Baran, Phil S. J Am Chem Soc [Image: see text] The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored. American Chemical Society 2016-06-10 2016-06-22 /pmc/articles/PMC4919752/ /pubmed/27284962 http://dx.doi.org/10.1021/jacs.6b04816 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 Martinez, Luisruben P.
Umemiya, Shigenobu
Wengryniuk, Sarah E.
Baran, Phil S.
11-Step Total Synthesis of Pallambins C and D
title 11-Step Total Synthesis of Pallambins C and D
title_full 11-Step Total Synthesis of Pallambins C and D
title_fullStr 11-Step Total Synthesis of Pallambins C and D
title_full_unstemmed 11-Step Total Synthesis of Pallambins C and D
title_short 11-Step Total Synthesis of Pallambins C and D
title_sort 11-step total synthesis of pallambins c and d
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4919752/
https://www.ncbi.nlm.nih.gov/pubmed/27284962
http://dx.doi.org/10.1021/jacs.6b04816
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