Complementary Stereocontrolled Approaches to 2-Pyrrolidinones Bearing a Vicinal Amino Diol Subunit with Three Continuous Chiral Centers: A Formal Asymmetric Synthesis of (−)-Detoxinine

We report herein two stereocomplementary approaches to erythro/trans and threo/cis vicinal amino diol
subunits containing 2-pyrrolidinones (9 and 10) starting from the known enamides 7, easily available
from malimides. The first approach consists of an epoxidation−reductive dehydroxylation procedure,
and the second one is based on hydroboration−oxidation reactions. Using the second method, a formal
asymmetric synthesis of (−)-detoxinine was achieved.