Journal article
Towards the synthesis of chiral isochromanquinones. The use of Corey–Bakshi–Shibata reductions
Tetrahedron Letters, Vol.43(23), pp.4199-4201
2002
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.
Details
- Title
- Towards the synthesis of chiral isochromanquinones. The use of Corey–Bakshi–Shibata reductions
- Authors/Creators
- C.B. de Koning (Author/Creator) - University of the WitwatersrandR.G.F. Giles (Author/Creator) - Murdoch UniversityI.R. Green (Author/Creator) - University of the Western CapeN.M. Jahed (Author/Creator) - University of the Western Cape
- Publication Details
- Tetrahedron Letters, Vol.43(23), pp.4199-4201
- Publisher
- Elsevier BV
- Identifiers
- 991005540418807891
- Copyright
- © 2002 Elsevier Science Ltd
- Murdoch Affiliation
- School of Chemical and Mathematical Science
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
- Domestic collaboration
- International collaboration
- Citation topics
- 1 Clinical & Life Sciences
- 1.219 Cancer Drugs
- 1.219.1527 Naphthoquinone Derivatives
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry