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Journal of the Chilean Chemical Society

On-line version ISSN 0717-9707

Abstract

ALARCON, JULIO; ALDERETE, JOEL B; AGUILA, SERGIO  and  PETER, MARTIN G. REGIO AND STEREOSELECTIVE HYDROXYLATION OF A-AGAROFURAN BY BIOTRANSFORMATION OF RHIZOPUS NIGRICANS. J. Chil. Chem. Soc. [online]. 2005, vol.50, n.4, pp.715-718. ISSN 0717-9707.  http://dx.doi.org/10.4067/S0717-97072005000400012.

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

Keywords : Agarofuran Synthesis; Celastraceae; Eudesmanes; Microbiological hydroxylation; Sesquiterpenes.

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