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

de Koning, C.B., Giles, R.G.F., Green, I.R. and Jahed, N.M. (2002) Towards the synthesis of chiral isochromanquinones. The use of Corey–Bakshi–Shibata reductions. Tetrahedron Letters, 43 (23). pp. 4199-4201.

Link to Published Version: http://dx.doi.org/10.1016/S0040-4039(02)00759-1
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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.

Publication Type: Journal Article
Murdoch Affiliation: School of Chemical and Mathematical Science
Publisher: Elsevier BV
Copyright: © 2002 Elsevier Science Ltd
URI: http://researchrepository.murdoch.edu.au/id/eprint/35534
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