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Ilicic Acid as a Natural Quiron for the Efficient Preparation of Bioactive α‐ and β‐Eudesmol

2009; Wiley; Volume: 2009; Issue: 21 Linguagem: Inglês

10.1002/ejoc.200900438

1434-193X

Alejandro F. Barrero, M. Mar Herrador, Pilar Arteaga, Julieta V. Catalán,

Synthesis and Biological Activity

Abstract An efficient procedure for the isolation of the sesquiterpene ilicic acid ( 3 ) on a multigram scale of extracts obtained from aerial parts of Inula viscosa (Asteraceae) was developed. Acid 3 is an appropriate starting material for short, enantiospecific syntheses of β‐eudesmol ( 1 ) and α‐eudesmol ( 2 ), natural products featuring significant antiangiogenic and anti‐Alzheimer properties. Synthesis of 1 was achieved in six steps and the synthesis of 2 in seven, producing overall yields of 52 and 41 %, respectively.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)