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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetals / chemistry*
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Ascomycota / chemistry
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Biological Products / isolation & purification
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Catalysis
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Cobalt / chemistry*
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Cyclohexanones / chemical synthesis*
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Cyclohexanones / chemistry
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Cyclohexanones / isolation & purification
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Ethylenediamines / chemistry*
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Molecular Structure
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Organometallic Compounds / chemistry*
Substances
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(4S,5S)-dihydroxycyclohexen-1-one
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Acetals
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Biological Products
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Cyclohexanones
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Ethylenediamines
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Organometallic Compounds
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Cobalt
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disalicylaldehyde ethylenediamine