Towards the synthesis of chiral isochromanquinones. The use of Corey-Bakshi-Shibata reductions

Abstract

(1R,3R,4S)-3,4-Dihydro-4-hydroxy-6-methoxy-1,3-dimethylisochroman-5,8-dione has been synthesized in 65% ee from (1R,3R,4S)-5-benzyloxy-3,4-dihydro-4-hydroxy-6-methoxy-1,3-dimethylisochroman by catalytic hydrogenolysis followed by Fremy's salt oxidation of the derived phenol. The latter isochroman was synthesized from a mercury(II) mediated oxidative cyclization of (R)-3-benzyloxy-4-methoxy-1-(1′-hydroxyethyl)-2-prop-1′- enylbenzene which in turn was obtained in 75% ee from the chiral reduction of 1-acetyl-3-benzyloxy-4-methoxy-2-prop-1′-enylbenzene with borane-methylsulfide complex in the presence of the Corey-Bakshi-Shibata catalyst. © 2002 Elsevier Science Ltd. All rights reserved.