Issue 17, 2004
From the journal:

Organic & Biomolecular Chemistry

The synthesis of ventiloquinone L, the monomer of cardinalin 3

Edwin M. Mmutlane,a   Joseph P. Michael,a   Ivan R. Greenb  and  Charles B. de Koning*a  

* Corresponding authors

a Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits, South Africa
E-mail: dekoning@aurum.chem.wits.ac.za
Fax: 27 + 11 + 717 6749
Tel: 27 + 11 + 717 6724

b Department of Chemistry, University of the Western Cape, Private Bag X17, Bellville, South Africa

Abstract

Readily available ethyl-4-acetoxy-6,8-dimethoxynaphthalene-2-carboxylate 27 was converted into 1-[3-allyl-4-(benzyloxy)-6,8-dimethoxy-2-naphthyl)-1-ethanol 31 in seven steps. Subjection of this compound to Wacker oxidation conditions provided 5-benzyloxy-7,9-dimethoxy-1,3-dimethyl-1H-benzo[g]isochromene 32 in good yield. Hydrogenation of the isochromene afforded (±)-cis-7,9-dimethoxy-1,3-dimethyl-1H-benzo[g]isochroman-5-ol 33 as the major product, which was readily converted into ventiloquinone L.

Graphical abstract: The synthesis of ventiloquinone L, the monomer of cardinalin 3

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Article information

DOI
https://doi.org/10.1039/B407208A
Article type
Paper
Submitted
14 May 2004
Accepted
17 Jun 2004
First published
02 Aug 2004

Org. Biomol. Chem., 2004,2, 2461-2470

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The synthesis of ventiloquinone L, the monomer of cardinalin 3

E. M. Mmutlane, J. P. Michael, I. R. Green and C. B. de Koning, Org. Biomol. Chem., 2004, 2, 2461 DOI: 10.1039/B407208A

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