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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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Autores principales: Shaik, Faruk Hasan, Kar, Gandhi Kumar
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
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.
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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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