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Total synthesis of Psymberin (Partial):
Reference: Rech, J. C.; Floreancig, P. E. Org. Lett. 2005, 7, 5175-5178. DOI
Keywords: O-H → O-SiMe2tBu • CarboxEster → Aldehyde • O-H → O-SiMe2tBu • O-H → O-SiEt3 • Ketone → EnolSilane • Diol-1,3 → Acetal • Ketone → Alkyl-OH • Ether-6 • O-SiMe2tBu → O-H • O-C(O)R → O-H • Diels-Alder, Allene • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Si-Allyl+Aldehyde • Aldehyde+Si-R • Benzene synthesis • Ozonolysis • Ozonolysis • Mukaiyama Aldol • Aldol-Si • Felkin-Anh • CompE+-Aldehyde/Ketone+Si-Allyl • CompRed-CarboxEster/CarboxEster+Al-H •
Reagents: HF·NEt3 • SiMe2tBu-OTf • AlHiBu2 • Chiral auxiliary-Boronate • SiMe2tBu-OTf • O3 • Allyl-SiR3 • Chiral auxiliary-Misc • SiEt3-Cl • SiMe3-OTf • BF3·OEt2 • Me2C(OMe)2 • TsOH • BH4-Na+ • O3 • Cyanide, trimethylsilyl • Acetic anhydride, Py • Fluoride, R4N+ • Carbonate, potassium • Crotyl-B(Ipc)2 • Lutidine • BF3·OEt2 • Lutidine •

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