Absolute stereochemistry of chinesin I and II

Abstract

The absolute stereochemistry of chinesin I and II has been elucidated by synthetic and spectroscopic experiments. Tetrahydrochinesin I was degraded with ozonolysis and converted into the cyclopentane derivative 5 whose absolute stereochemistry was elucidated by synthesis from (–)-linalool. Degradation of chinesin I with H₂SO₄ gave (S)-2-methylbutyric acid. Finally, the absolute configuration of chinesin I was established as 4R, 8S, 9R, 12R, 24S.