Journal
TETRAHEDRON
Volume 57, Issue 33, Pages 7127-7135Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00631-7
Keywords
mastigophorene; herbertane-type sesquiterpene; Heck reaction; horseradish peroxidase; neuroprotective activity
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(-)-Herbertenediol (3) which is regarded as a biosynthetic precursor of mastigophorenes A and B has been effectively synthesized from (R)-1,2-dimethyl-2-cyclopentene carboxylic acid by applying an intramolecular Heck reaction to the construction of the quaternary carbon center, and then horseradish peroxidase-catalyzed oxidative coupling of 3 has given rise to (-)-mastigophorenes A and B. Mastigophorenes A and B have been found to exhibit significant neuroprotective activity in primary cultures of fetal rat cortical neurons. (C) 2001 Elsevier Science Ltd. All rights reserved.
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