Biomimetic studies towards the cardinalins: synthesis of (+)-ventiloquinone L and an unusual dimerisation

Studies towards the biomimetic synthesis of cardinalin 3 are described. Despite the successful enantioselective synthesis of the monomeric pyranonaphthoquinone ventiloquinone L, it subsequently failed to undergo a proposed biomimetic homodimerisation to cardinalin 3 using a range of oxidants. Howeve...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (12), p.2599-2603
Main Authors: Sperry, Jonathan, Sejberg, Jimmy J P, Stiemke, Frank M, Brimble, Margaret A
Format: Article
Language:English
Subjects:
Benzofurans - chemistry
Benzoquinones - chemical synthesis
Benzoquinones - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Biomimetics
Dimerization
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
Plant Roots - chemistry
Pyrans - chemical synthesis
Pyrans - chemistry
Rhamnaceae - chemistry
Stereoisomerism
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Summary:Studies towards the biomimetic synthesis of cardinalin 3 are described. Despite the successful enantioselective synthesis of the monomeric pyranonaphthoquinone ventiloquinone L, it subsequently failed to undergo a proposed biomimetic homodimerisation to cardinalin 3 using a range of oxidants. However, treatment of a related naphthopyran with cerium ammonium nitrate (CAN) facilitated a tandem biaryl bond formation-oxidative demethylation sequence furnishing a dimeric pyranonaphthoquinone that had exclusively dimerised at C6. The nature of this unusual sequence is discussed and the product subsequently converted to the C6 regioisomer of cardinalin 3.
ISSN:1477-0520
1477-0539
DOI:10.1039/b905077a