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

(1 R,3 R,4 S)-3,4-Dihydro-4-hydroxy-6-methoxy-1,3-dimethylisochroman-5,8-dione has been synthesized in 65% ee from (1 R,3 R,4 S)-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 is...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2002-06, Vol.43 (23), p.4199-4201
Main Authors: de Koning, Charles B, Giles, Robin G.F, Green, Ivan R, Jahed, Nazeem M
Format: Article
Language:English
Subjects:
chiral reduction
isochromanquinones
mercury(II) mediated oxidative cyclisation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:(1 R,3 R,4 S)-3,4-Dihydro-4-hydroxy-6-methoxy-1,3-dimethylisochroman-5,8-dione has been synthesized in 65% ee from (1 R,3 R,4 S)-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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)00759-1