1986
DOI: 10.1021/ja00274a050
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Total synthesis of (-)-coriolin

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Cited by 71 publications
(45 citation statements)
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“…As outlined in Scheme 3, the synthesis began with selenium dioxide elimination [13,14] from the selenide 7, [9,15,16] followed by oxidative rearrangement [17] of the allylic alcohol 8 by treatment with pyridinium chlorochromate. This gave rise to the α,β-unsaturated ketone 9, which was isolated pure in good yield (92%).…”
Section: Resultsmentioning
confidence: 99%
“…As outlined in Scheme 3, the synthesis began with selenium dioxide elimination [13,14] from the selenide 7, [9,15,16] followed by oxidative rearrangement [17] of the allylic alcohol 8 by treatment with pyridinium chlorochromate. This gave rise to the α,β-unsaturated ketone 9, which was isolated pure in good yield (92%).…”
Section: Resultsmentioning
confidence: 99%
“…[164,165] Ein mit 106 verwandtes Diketon diente nach dreifacher Methylierung als Ausgangsmaterial in einer Synthese von (À)-Coriolin (113). [166] Weitere Zugänge zu (AE )-Coriolin (113) [173] Sehr häufig dient die Diels-Alder-Reaktion als Zugangsweg zu den als Ausgangsmaterial für die Oxadi-p-Methanumlagerung eingesetzten Bicyclo[2.2.2]octenonen. Die dafür notwendigen Cyclohexadiene lassen sich auf vielfältigem Weg herstellen, wobei aus jüngster Zeit die Studien von Singh et al [167] und von Banwell et al [169] [174] Synthesen von (AE )-D 9(12) -Capnellen [175] und des Lycopodium-Alkaloids (AE )-Magellanin [176] ]heptangerüst der Tricyclenterpenoide.…”
Section: Oxadi-p-methanumlagerungenunclassified
“…6 The C1-C5 segment was developed from the commercially available (S)-(-)-citronellic acid as shown in Scheme III. Oxidative cleavage of (S)-(-)-citronellic acid with OsO 4 /NaIO 4 to give (S)-3-methyl-6-oxo-hexanoic acid 7 and subsequent reduction of the carbonyl group with NaBH 4 afforded (S)-6-hydroxy-3-methylhexanoic acid (6) as a colorless liquid in 80% yield. A two-step sequence involving iodination (NaI, TMSCl, CH 3 CN) 8 and elimination (t-BuOK, THF) 9 produced (S)-3-methylhex-5-enoic acid (7) in an excellent yield (98%).…”
Section: Resultsmentioning
confidence: 99%
“…Oxidative cleavage of (S)-(-)-citronellic acid with OsO 4 /NaIO 4 to give (S)-3-methyl-6-oxo-hexanoic acid 7 and subsequent reduction of the carbonyl group with NaBH 4 afforded (S)-6-hydroxy-3-methylhexanoic acid (6) as a colorless liquid in 80% yield. A two-step sequence involving iodination (NaI, TMSCl, CH 3 CN) 8 and elimination (t-BuOK, THF) 9 produced (S)-3-methylhex-5-enoic acid (7) in an excellent yield (98%). The spectral integration ratio for the olefinic protons which appeared at d 5.82-5.72 (m, 1H) and d 5.06-5.02 (m, 2H) was 1:2, suggesting a terminal alkenoid geometry in the double bond.…”
Section: Resultsmentioning
confidence: 99%