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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 • O-SiPh2tBu → O-H • Alkyl-X → Alkyl-SeR • Mitsunobu → SeR • Selenide → Selenoxide • CarboxEster → Alkyl-OH • Favorskii • Cyclopentane • Enone epoxidation, nucleophilic • CompOx-Enone/Alkene+ROOH • Selenoxide-Ei → Ene • RCM → Ring-C • Cycloheptane • Epoxidation, peracid • CompOx-Alkene/Enoate+Peracid • Epoxide reduction • Alkyl-OH → CarboxAcid • Alkyl-OSiR3 → Ketone • Felkin-Anh • B-Allyl+Aldehyde • Lactone-5 • Epoxide → Chlorohydrin • Mechanism • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde •
Reagents: H2O2, NaOH • Chloride, lithium • SiMe2tBu-OTf • NaOMe • AlH4-Li+ • DMSO, (COCl)2 (Swern) • Carvone • Fluoride, R4N+ • Selenocyanate, o-nitrophenyl • PBu3 • H2O2 • Grubbs II • AlHiBu2 • BH(Et)3-Li+ • MnO2 • Perbenzoic acid, 3-chloro • Cr2O7·2PyH (PDC) • SiMe3-Cl • Acetic acid, trifluoro • BF3·OEt2

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