Abstract
Reaction of the (1S)-allylic hydroxy phosphonate 1(S) with methyl chloroformate in pyridine yields the corresponding carbonate 3(S). The carbonate 3(S) undergoes a palladium-catalyzed arylation with p-tolyl tributylstannane to give both the 1E and 1Z vinyl phosphonates 6 (85:15). The E and Z vinyl phosphonates 6 were shown to have the opposite configuration at C-3. The major vinyl phosphonate isomer (3S,1E), was converted to (3S)-3-(p-tolyl)-butanal 8(S), completing a formal total synthesis of (S)-ar-turmerone 5a.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Allyl Compounds / chemical synthesis*
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Allyl Compounds / chemistry
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Catalysis
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Ketones / chemical synthesis*
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Ketones / chemistry
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Models, Chemical
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Molecular Structure
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Organophosphonates / chemical synthesis*
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Organophosphonates / chemistry
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Palladium / chemistry*
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Sesquiterpenes
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Stereoisomerism
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Structure-Activity Relationship
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Toluene / analogs & derivatives*
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Toluene / chemical synthesis*
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Toluene / chemistry
Substances
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Allyl Compounds
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Ketones
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Organophosphonates
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Sesquiterpenes
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ar-turmerone
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Toluene
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Palladium