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cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin
We have synthesized a series of cis-6a,7,8,12b-tetrahydro-6H-naphtho[2,1-c]chromen-6a-ols as B-ring-modified analogues of (±)-brazilin. A completely regio- and cis-diastereoselective intramolecular Friedel–Crafts epoxy–arene cyclization of 1-tetralone-derived glycidyl ethers catalyzed by Brønsted ac...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Beilstein-Institut
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238543/ https://www.ncbi.nlm.nih.gov/pubmed/28144354 http://dx.doi.org/10.3762/bjoc.12.280 |
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author | Gogoi, Dimpee Devi, Runjun Pahari, Pallab Sarma, Bipul Das, Sajal Kumar |
author_facet | Gogoi, Dimpee Devi, Runjun Pahari, Pallab Sarma, Bipul Das, Sajal Kumar |
author_sort | Gogoi, Dimpee |
collection | PubMed |
description | We have synthesized a series of cis-6a,7,8,12b-tetrahydro-6H-naphtho[2,1-c]chromen-6a-ols as B-ring-modified analogues of (±)-brazilin. A completely regio- and cis-diastereoselective intramolecular Friedel–Crafts epoxy–arene cyclization of 1-tetralone-derived glycidyl ethers catalyzed by Brønsted acids was used as the key step. Our worries concerning the formation of cis–trans product mixtures and their probable conversion to naphthopyran derivatives via dehydration of the tertiary hydroxy group were laid to rest. Additionally, the angular hydroxy group of one of the synthesized products has been reductively removed by a diastereoselective method which should be useful in future for preparing libraries of chroman-fused tetralins with trans-stereochemistry at the ring junction. |
format | Online Article Text |
id | pubmed-5238543 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-52385432017-01-31 cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin Gogoi, Dimpee Devi, Runjun Pahari, Pallab Sarma, Bipul Das, Sajal Kumar Beilstein J Org Chem Letter We have synthesized a series of cis-6a,7,8,12b-tetrahydro-6H-naphtho[2,1-c]chromen-6a-ols as B-ring-modified analogues of (±)-brazilin. A completely regio- and cis-diastereoselective intramolecular Friedel–Crafts epoxy–arene cyclization of 1-tetralone-derived glycidyl ethers catalyzed by Brønsted acids was used as the key step. Our worries concerning the formation of cis–trans product mixtures and their probable conversion to naphthopyran derivatives via dehydration of the tertiary hydroxy group were laid to rest. Additionally, the angular hydroxy group of one of the synthesized products has been reductively removed by a diastereoselective method which should be useful in future for preparing libraries of chroman-fused tetralins with trans-stereochemistry at the ring junction. Beilstein-Institut 2016-12-21 /pmc/articles/PMC5238543/ /pubmed/28144354 http://dx.doi.org/10.3762/bjoc.12.280 Text en Copyright © 2016, Gogoi et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 | Letter Gogoi, Dimpee Devi, Runjun Pahari, Pallab Sarma, Bipul Das, Sajal Kumar cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin |
title | cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin |
title_full | cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin |
title_fullStr | cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin |
title_full_unstemmed | cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin |
title_short | cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin |
title_sort | cis-diastereoselective synthesis of chroman-fused tetralins as b-ring-modified analogues of brazilin |
topic | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238543/ https://www.ncbi.nlm.nih.gov/pubmed/28144354 http://dx.doi.org/10.3762/bjoc.12.280 |
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