Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A.

J Org Chem

Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071, Granada, Spain.

Published: April 2007

Hyptatic acid-A (32), a 2alpha,3beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

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http://dx.doi.org/10.1021/jo070116eDOI Listing

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