REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS

A new synthesis of 9a-hydroxy-a-agarofuran (6a) is described, using a microbiological hydroxylation a-agarofuran (5) as the key reaction. The stereochemistry of the biohydroxylation was determined on the basis of a NOESY-experiment and GIAO calculations at the B3LYP/cc-pVDZ level. A strong g-effect...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	ALARCÓN,JULIO, ALDERETE,JOEL B, AGUILA,SERGIO, PETER,MARTIN G
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2005
Materias:	Agarofuran Synthesis Celastraceae Eudesmanes Microbiological hydroxylation Sesquiterpenes
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072005000400012
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:scielo:S0717-97072005000400012
record_format	dspace
spelling	oai:scielo:S0717-970720050004000122006-04-19REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANSALARCÓN,JULIOALDERETE,JOEL BAGUILA,SERGIOPETER,MARTIN G Agarofuran Synthesis Celastraceae Eudesmanes Microbiological hydroxylation Sesquiterpenes A new synthesis of 9a-hydroxy-a-agarofuran (6a) is described, using a microbiological hydroxylation a-agarofuran (5) as the key reaction. The stereochemistry of the biohydroxylation was determined on the basis of a NOESY-experiment and GIAO calculations at the B3LYP/cc-pVDZ level. A strong g-effect was observed at C15 of the agarofuran ring which was correctly predicted by the GIAO-B3LYP calculationsinfo:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.50 n.4 20052005-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072005000400012en10.4067/S0717-97072005000400012
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Agarofuran Synthesis Celastraceae Eudesmanes Microbiological hydroxylation Sesquiterpenes
spellingShingle	Agarofuran Synthesis Celastraceae Eudesmanes Microbiological hydroxylation Sesquiterpenes ALARCÓN,JULIO ALDERETE,JOEL B AGUILA,SERGIO PETER,MARTIN G REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS
description	A new synthesis of 9a-hydroxy-a-agarofuran (6a) is described, using a microbiological hydroxylation a-agarofuran (5) as the key reaction. The stereochemistry of the biohydroxylation was determined on the basis of a NOESY-experiment and GIAO calculations at the B3LYP/cc-pVDZ level. A strong g-effect was observed at C15 of the agarofuran ring which was correctly predicted by the GIAO-B3LYP calculations
author	ALARCÓN,JULIO ALDERETE,JOEL B AGUILA,SERGIO PETER,MARTIN G
author_facet	ALARCÓN,JULIO ALDERETE,JOEL B AGUILA,SERGIO PETER,MARTIN G
author_sort	ALARCÓN,JULIO
title	REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS
title_short	REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS
title_full	REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS
title_fullStr	REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS
title_full_unstemmed	REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS
title_sort	regio and stereoselective hydroxylation of a-agarofuran by biotransformation of rhizopus nigricans
publisher	Sociedad Chilena de Química
publishDate	2005
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072005000400012
work_keys_str_mv	AT alarconjulio regioandstereoselectivehydroxylationofaagarofuranbybiotransformationofrhizopusnigricans AT alderetejoelb regioandstereoselectivehydroxylationofaagarofuranbybiotransformationofrhizopusnigricans AT aguilasergio regioandstereoselectivehydroxylationofaagarofuranbybiotransformationofrhizopusnigricans AT petermarting regioandstereoselectivehydroxylationofaagarofuranbybiotransformationofrhizopusnigricans
_version_	1718445355424546816

REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS

Ejemplares similares