image

Total synthesis of Chinensiolide B:
Reference: Elford, T. G. Hall, D. G. J. Am. Chem. Soc. 2010, 132, 1488. DOI
Keywords: O-H -> O-SiMe2tBu • CarboxEster -> Alkyl-OH • Alkyl-OH -> Aldehyde • O-SiPh2tBu -> O-H • Alkyl-OH -> Alkyl-SeR • CarboxEster -> Alkyl-OH • Favorski • Epoxidation, nucleophilic Enone • Selenoxide-Ei -> Ene • RCM -> Ring-C • Epoxidation, peracid • Epoxide reduction • Alkyl-OH -> CarboxAcid • Alkyl-OSiR3 -> Ketone • Felkin-Anh • B-Allyl+Aldehyde • Lactone-5 • Epoxide -> Chlorohydrin •
Reagents: H2O2, NaOH • Chloride, lithium • SiMe2tBu-OTf • NaOMe • AlH4-Li+ • DMSO, (COCl)2 • Carvone • Fluoride, Bu4N+ • Selenocyanate, o-nitrophenyl • PBu3 • H2O2 • Grubbs II • AlHiBu2 • MnO2 • Perbenzoic acid, 3-chloro • Cr2O7·2PyH (PDC) • SiMe3-Cl • Acetic acid, trifluoro • BF3·OEt2

Syntheses Home