Synthesis of Optically Active Methyl 7β-Hydroxykaurenoate with Potent Neuroprotective Activity

Masahiro Toyota; Kiminori Matsuura; Masahiro Yokota; Manami Kimura; Masahiro Yonaga; Hachiro Sugimoto; Masataka Ihara

doi:10.1248/cpb.52.1153

Communications to the Editor

Synthesis of Optically Active Methyl 7β-Hydroxykaurenoate with Potent Neuroprotective Activity

Masahiro Toyota, Kiminori Matsuura, Masahiro Yokota, Manami Kimura, Masahiro Yonaga, Hachiro Sugimoto, Masataka Ihara

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Keywords: kaurene diterpenoid, neuroprotective activity, chiral synthesis, radical cyclization

JOURNAL FREE ACCESS

2004 Volume 52 Issue 9 Pages 1153-1154

DOI https://doi.org/10.1248/cpb.52.1153

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Abstract

(−)-Methyl 7β-hydroxykaurenoate (3) and its 4-demethyl acetate (−)-4 were both synthesized via methods that contained radical cyclization and intramolecular Diels-Alder reactions as key steps. Both compounds displayed potent neuroprotective activity against N-methyl-D-aspartate toxicity in cultured cortical neurons.

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