An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil

An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil

cis-4a-Methyloctahydrophenanthrene (1) was prepared in 8 steps (23% overall yield) from 2-bromophenyl)acetic acid (3) and cyclohexane-1,3-dione (6). A highly cis-diastereoselective Michael-type Heck coupling served as the key step in the assembly of the tricyclic skeleton. This compound 1 was used a...

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Main Authors: Rodrigues Denise C., Meijere Armin de, Marsaioli Anita J.
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2002-01-01
Series:Journal of the Brazilian Chemical Society
Subjects:
cis-4a-Methyloctahydrophenanthrene
biomarker
Carmopolis petroleum
Sergipe-Alagoas Basin
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000500020
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spelling doaj-612740aa20284a0bb3ab302c39f240a22020-11-24T21:38:17ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532002-01-01135664668An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in BrazilRodrigues Denise C.Meijere Armin deMarsaioli Anita J.cis-4a-Methyloctahydrophenanthrene (1) was prepared in 8 steps (23% overall yield) from 2-bromophenyl)acetic acid (3) and cyclohexane-1,3-dione (6). A highly cis-diastereoselective Michael-type Heck coupling served as the key step in the assembly of the tricyclic skeleton. This compound 1 was used as gas chromatography standard which allowed the unequivocal identification of a minor biomarker present in Carmopolis oil from the Sergipe-Alagoas Basin in Brazil.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000500020cis-4a-MethyloctahydrophenanthrenebiomarkerCarmopolis petroleumSergipe-Alagoas Basin
collection DOAJ
language English
format Article
sources DOAJ
author Rodrigues Denise C.
Meijere Armin de
Marsaioli Anita J.
spellingShingle Rodrigues Denise C.
Meijere Armin de
Marsaioli Anita J.
An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil
Journal of the Brazilian Chemical Society
cis-4a-Methyloctahydrophenanthrene
biomarker
Carmopolis petroleum
Sergipe-Alagoas Basin
author_facet Rodrigues Denise C.
Meijere Armin de
Marsaioli Anita J.
author_sort Rodrigues Denise C.
title An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil
title_short An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil
title_full An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil
title_fullStr An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil
title_full_unstemmed An Alternative Synthetic Access to cis-4a-Methyloctahydrophenanthrene, a Biomarker of Sergipe-Alagoas Basin Petroleum in Brazil
title_sort alternative synthetic access to cis-4a-methyloctahydrophenanthrene, a biomarker of sergipe-alagoas basin petroleum in brazil
publisher Sociedade Brasileira de Química
series Journal of the Brazilian Chemical Society
issn 0103-5053
publishDate 2002-01-01
description cis-4a-Methyloctahydrophenanthrene (1) was prepared in 8 steps (23% overall yield) from 2-bromophenyl)acetic acid (3) and cyclohexane-1,3-dione (6). A highly cis-diastereoselective Michael-type Heck coupling served as the key step in the assembly of the tricyclic skeleton. This compound 1 was used as gas chromatography standard which allowed the unequivocal identification of a minor biomarker present in Carmopolis oil from the Sergipe-Alagoas Basin in Brazil.
topic cis-4a-Methyloctahydrophenanthrene
biomarker
Carmopolis petroleum
Sergipe-Alagoas Basin
url http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000500020
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AT meijerearminde analternativesyntheticaccesstocis4amethyloctahydrophenanthreneabiomarkerofsergipealagoasbasinpetroleuminbrazil
AT marsaiolianitaj analternativesyntheticaccesstocis4amethyloctahydrophenanthreneabiomarkerofsergipealagoasbasinpetroleuminbrazil
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