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Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids
Synthesis of phenanthro[1,2-b]furan-10,11-dione, the core nucleus present in Tanshinone-I is described in 8–10 steps starting from 2-bromo-3,4-dihydro-1-naphthaldehyde. The bromoaldehyde was converted to methyl 2-(2-bromo-1-naphthyl)acetate or 2-(2-bromo-1-naphthyl)acetonitrile following the protoco...
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2779660/ https://www.ncbi.nlm.nih.gov/pubmed/19936265 http://dx.doi.org/10.3762/bjoc.5.47 |
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author | Shaik, Faruk Hasan Kar, Gandhi Kumar |
author_facet | Shaik, Faruk Hasan Kar, Gandhi Kumar |
author_sort | Shaik, Faruk Hasan |
collection | PubMed |
description | Synthesis of phenanthro[1,2-b]furan-10,11-dione, the core nucleus present in Tanshinone-I is described in 8–10 steps starting from 2-bromo-3,4-dihydro-1-naphthaldehyde. The bromoaldehyde was converted to methyl 2-(2-bromo-1-naphthyl)acetate or 2-(2-bromo-1-naphthyl)acetonitrile following the protocol of functional group transformations. Subsequent Suzuki coupling of this ester/nitrile derivative with furan-2-boronic acid produced [2-(2-furyl)-1-naphthyl]acetic ester/nitrile which on hydrolysis furnished the corresponding acid derivative. Cyclization of the acid followed by oxidation of the phenol, with Fremy’s salt, produced the tetra-cyclic furoquinone, phenanthro[1,2-b]furan-10,11-dione. This method has also been extended for the synthesis of the tricyclic furoquinone, naphtho[1,2-b]furan-4,5-dione. |
format | Text |
id | pubmed-2779660 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-27796602009-11-20 Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids Shaik, Faruk Hasan Kar, Gandhi Kumar Beilstein J Org Chem Full Research Paper Synthesis of phenanthro[1,2-b]furan-10,11-dione, the core nucleus present in Tanshinone-I is described in 8–10 steps starting from 2-bromo-3,4-dihydro-1-naphthaldehyde. The bromoaldehyde was converted to methyl 2-(2-bromo-1-naphthyl)acetate or 2-(2-bromo-1-naphthyl)acetonitrile following the protocol of functional group transformations. Subsequent Suzuki coupling of this ester/nitrile derivative with furan-2-boronic acid produced [2-(2-furyl)-1-naphthyl]acetic ester/nitrile which on hydrolysis furnished the corresponding acid derivative. Cyclization of the acid followed by oxidation of the phenol, with Fremy’s salt, produced the tetra-cyclic furoquinone, phenanthro[1,2-b]furan-10,11-dione. This method has also been extended for the synthesis of the tricyclic furoquinone, naphtho[1,2-b]furan-4,5-dione. Beilstein-Institut 2009-09-29 /pmc/articles/PMC2779660/ /pubmed/19936265 http://dx.doi.org/10.3762/bjoc.5.47 Text en Copyright © 2009, Shaik and Kar https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Shaik, Faruk Hasan Kar, Gandhi Kumar Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids |
title | Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids |
title_full | Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids |
title_fullStr | Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids |
title_full_unstemmed | Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids |
title_short | Studies on polynuclear furoquinones. Part 1: Synthesis of tri- and tetra-cyclic furoquinones simulating BCD/ABCD ring system of furoquinone diterpenoids |
title_sort | studies on polynuclear furoquinones. part 1: synthesis of tri- and tetra-cyclic furoquinones simulating bcd/abcd ring system of furoquinone diterpenoids |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2779660/ https://www.ncbi.nlm.nih.gov/pubmed/19936265 http://dx.doi.org/10.3762/bjoc.5.47 |
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