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Diastereoselective Synthesis of (±)-epi-Subincanadine C
[Image: see text] Starting from indolylmaleimide, concise and efficient total synthesis of (±)-epi-subincanadine C was described via stereoselective Wittig olefination, base-induced selective mono-prenylation, regioselective Grignard reaction, diastereoselective Pictet–Spengler cyclization, regiosel...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641871/ https://www.ncbi.nlm.nih.gov/pubmed/31458740 http://dx.doi.org/10.1021/acsomega.8b00587 |
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author | Kalshetti, Manojkumar G. Argade, Narshinha P. |
author_facet | Kalshetti, Manojkumar G. Argade, Narshinha P. |
author_sort | Kalshetti, Manojkumar G. |
collection | PubMed |
description | [Image: see text] Starting from indolylmaleimide, concise and efficient total synthesis of (±)-epi-subincanadine C was described via stereoselective Wittig olefination, base-induced selective mono-prenylation, regioselective Grignard reaction, diastereoselective Pictet–Spengler cyclization, regioselective oxidative carbon–carbon double-bond cleavage, one-pot reductions, and intramolecular cyclization pathway. An attempted synthesis of (±)-subincanadine C via diastereoselective Grignard addition to the α,β-unsaturated γ-lactam or diastereoselective reduction of a carbon–carbon double bond also resulted in yet another route to (±)-epi-subincanadine C. |
format | Online Article Text |
id | pubmed-6641871 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66418712019-08-27 Diastereoselective Synthesis of (±)-epi-Subincanadine C Kalshetti, Manojkumar G. Argade, Narshinha P. ACS Omega [Image: see text] Starting from indolylmaleimide, concise and efficient total synthesis of (±)-epi-subincanadine C was described via stereoselective Wittig olefination, base-induced selective mono-prenylation, regioselective Grignard reaction, diastereoselective Pictet–Spengler cyclization, regioselective oxidative carbon–carbon double-bond cleavage, one-pot reductions, and intramolecular cyclization pathway. An attempted synthesis of (±)-subincanadine C via diastereoselective Grignard addition to the α,β-unsaturated γ-lactam or diastereoselective reduction of a carbon–carbon double bond also resulted in yet another route to (±)-epi-subincanadine C. American Chemical Society 2018-05-17 /pmc/articles/PMC6641871/ /pubmed/31458740 http://dx.doi.org/10.1021/acsomega.8b00587 Text en Copyright © 2018 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 | Kalshetti, Manojkumar G. Argade, Narshinha P. Diastereoselective Synthesis of (±)-epi-Subincanadine C |
title | Diastereoselective Synthesis of (±)-epi-Subincanadine C |
title_full | Diastereoselective Synthesis of (±)-epi-Subincanadine C |
title_fullStr | Diastereoselective Synthesis of (±)-epi-Subincanadine C |
title_full_unstemmed | Diastereoselective Synthesis of (±)-epi-Subincanadine C |
title_short | Diastereoselective Synthesis of (±)-epi-Subincanadine C |
title_sort | diastereoselective synthesis of (±)-epi-subincanadine c |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641871/ https://www.ncbi.nlm.nih.gov/pubmed/31458740 http://dx.doi.org/10.1021/acsomega.8b00587 |
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