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- W1999452489 abstract "Abstract Authentic α‐santolinenone ( = (+)‐(4 R )‐1(7)‐ p ‐menthen‐2‐one; (+)‐ 1 ) is made available for the the first time in 30% overall yield from (+)‐(4 R )‐ p ‐menthene ((+)‐ 2 ) via the diastereoisomeric allylic alcohols (+)‐ 4a /(+)‐ 4b , which are oxidized to (+)‐ 1 with Ag 2 CO 3 / Celite . Yields are good, except for the last stage; indeed, only alcohol (+)‐ 4a , with equatorial OH‐group, undergoes oxidation, and (+)‐ 1 is partly substracted via a hetero Diels‐Alder dimerization giving a mixture of the diastereoisomeric dihydropyrans (+)‐ 5a /(+)‐ 5b . When Cr(VI) reagents ae used, (+)‐ 4a /(+)‐ 4b mainly give phellandral ( 6 ) and carvotanacetone ( 7 ), NnO 2 reacts too sluggishly with (+)‐ 4a /(+)‐ 4b . A camphor pyrolyzate, previously thought to be 1 must be a different compound, probably 7 ." @default.
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- W1999452489 date "1984-08-08" @default.
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- W1999452489 title "Synthesis of the Alleged Natural Monoterpenoid ?-Santolinenone" @default.
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- W1999452489 doi "https://doi.org/10.1002/hlca.19840670511" @default.
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