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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...

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Autores principales: Kalshetti, Manojkumar G., Argade, Narshinha P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
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.
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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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