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ChemicalBook CAS DataBase List STIGMATELLIN
91682-96-1

STIGMATELLIN synthesis

12synthesis methods
104701-95-3 Synthesis
[(2E,4E)-4-Methyl-2,4-hexadienyl]phosphonic Acid Diethyl Ester

104701-95-3
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4H-1-Benzopyran-2-heptanal, 8-hydroxy-α,γ,5,7-tetramethoxy-β,δ,3-trimethyl-4-oxo-, (αR,βS,δS,γS)-

276690-23-4
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Yield:91682-96-1 77%

Reaction Conditions:

Stage #1: (2E,4E)-4-Methylhexa-2,4-dienylphosphonic acid diethylesterwith lithium diisopropyl amide in tetrahydrofuran;hexane at -78; for 15 h;Metallation;
Stage #2: (2R,3S,4S,5S)-7-[8-hydroxy-5,7-dimethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanal in tetrahydrofuran;hexane at -78 - 20;Condensation;Horner-Wadsworth-Emmons reaction;

References:

Enders, Dieter;Geibel, Gunter;Osborne, Simon [Chemistry - A European Journal,2000,vol. 6,# 8,p. 1302 - 1309]

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