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Catalytic asymmetric synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one and use in natural product synthesis
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| Journal | Organic and Biomolecular Chemistry |
|---|---|
| Date | E-pub ahead of print - 20 Aug 2012 |
| Date | Published (current) - 14 Oct 2012 |
| Issue number | 38 |
| Volume | 10 |
| Number of pages | 3 |
| Pages (from-to) | 7666-8 |
| Early online date | 20/08/12 |
| Original language | English |
Abstract
Due to the lack of availability of unnatural (+)-quinic acid as a starting material, a 6-step synthesis of butane diacetal-protected (4S,5S)-dihydroxycyclohexen-1-one (formally derived from (+)-quinic acid) has been devised. The key catalytic asymmetric step involves a chiral Co-salen-catalysed epoxide ring-opening reaction. (4S,5S)-Dihydroxycyclohexen-1-one was utilised in the synthesis of two cyclohexenone natural products isolated from the mycelia of Lasiodiplodia theobromae.
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