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Stereoselective Synthesis of the C1–C16 Fragment of the Purported Structure of Formosalide B
[Image: see text] The first stereoselective synthesis of the C1–C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting f...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7203982/ https://www.ncbi.nlm.nih.gov/pubmed/32391510 http://dx.doi.org/10.1021/acsomega.0c01474 |
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author | Gajula, Srinivas Vishnu V. Reddy, Aedula Reddy, D. Prabhakar Yadav, Jhillu S. Mohapatra, Debendra K. |
author_facet | Gajula, Srinivas Vishnu V. Reddy, Aedula Reddy, D. Prabhakar Yadav, Jhillu S. Mohapatra, Debendra K. |
author_sort | Gajula, Srinivas |
collection | PubMed |
description | [Image: see text] The first stereoselective synthesis of the C1–C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting from two cheap and commercially available 1,5-pentanediol and l-glutamic acid, following a convergent approach. The key steps involve in this synthesis are Horner–Wadsworth–Emmons reaction, Sharpless asymmetric dihydroxylation, and acid-mediated ketalization to assemble the substituted THP ring, one-pot Sharpless dihydroxylation–S(N)2-type cyclization, and Wittig homologation to construct the THF derivative. |
format | Online Article Text |
id | pubmed-7203982 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-72039822020-05-08 Stereoselective Synthesis of the C1–C16 Fragment of the Purported Structure of Formosalide B Gajula, Srinivas Vishnu V. Reddy, Aedula Reddy, D. Prabhakar Yadav, Jhillu S. Mohapatra, Debendra K. ACS Omega [Image: see text] The first stereoselective synthesis of the C1–C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting from two cheap and commercially available 1,5-pentanediol and l-glutamic acid, following a convergent approach. The key steps involve in this synthesis are Horner–Wadsworth–Emmons reaction, Sharpless asymmetric dihydroxylation, and acid-mediated ketalization to assemble the substituted THP ring, one-pot Sharpless dihydroxylation–S(N)2-type cyclization, and Wittig homologation to construct the THF derivative. American Chemical Society 2020-04-23 /pmc/articles/PMC7203982/ /pubmed/32391510 http://dx.doi.org/10.1021/acsomega.0c01474 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 | Gajula, Srinivas Vishnu V. Reddy, Aedula Reddy, D. Prabhakar Yadav, Jhillu S. Mohapatra, Debendra K. Stereoselective Synthesis of the C1–C16 Fragment of the Purported Structure of Formosalide B |
title | Stereoselective Synthesis of the C1–C16 Fragment
of the Purported Structure of Formosalide B |
title_full | Stereoselective Synthesis of the C1–C16 Fragment
of the Purported Structure of Formosalide B |
title_fullStr | Stereoselective Synthesis of the C1–C16 Fragment
of the Purported Structure of Formosalide B |
title_full_unstemmed | Stereoselective Synthesis of the C1–C16 Fragment
of the Purported Structure of Formosalide B |
title_short | Stereoselective Synthesis of the C1–C16 Fragment
of the Purported Structure of Formosalide B |
title_sort | stereoselective synthesis of the c1–c16 fragment
of the purported structure of formosalide b |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7203982/ https://www.ncbi.nlm.nih.gov/pubmed/32391510 http://dx.doi.org/10.1021/acsomega.0c01474 |
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