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Total synthesis of Roflamycoin (Part 1):
Reference: Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. DOI
Keywords: Li/Sn -> Li-Dithiane • Li-Dithiane+Alkyl-X • Hydroboration Alkene • Pd/B-Alkyl+Vinyl-X • Suzuki coupling • Alkene cleavage • Diol-1,2 cleavage • O-H -> O-SiMe2tBu • Alkene cleavage • Diol-1,2 cleavage • CarboxEster -> Aldehyde • Aldehyde -> Cyanohydrin • Diol -> Ketal • Diol -> Ketal • Diol -> Ketal • Ketal(thio) -> Ketone • Petasis reagent • Ketone -> C=CH2 • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Aldol-Si • Li-Ether+Epoxide • Epoxide+Li-R • Li-Dithiane+Epoxide •
Reagents: BuLi(n) • Me2C(OMe)2 • Camphor sulfonic acid • Hg(ClO4)2 • TiCp2Me2 • OsO4, NMO • Camphor sulfonic acid • Me2C(OMe)2 • BH-BBN • Pd(PPh3)4 • Hydroxide, sodium • OsO4, NMO • Periodate, sodium • Allyl-B(Ipc)2 • H2O2, NaOH • SiMe2tBu-OTf • OsO4, NMO • Periodate, sodium • CH2=C(OR)(OSiR'3) • AlHiBu2 • Cyanide, trimethylsilyl • Camphor sulfonic acid • Me2C(OMe)2 • Carbonate, calcium • Chiral catalyst • BF3·OEt2

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