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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...

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Autores principales: Gogoi, Dimpee, Devi, Runjun, Pahari, Pallab, Sarma, Bipul, Das, Sajal Kumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
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.
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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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