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Total synthesis of Didehyroacutiphycin:
Reference: Smith, A. B.; Chen, S. S.-Y.; Nelsom, F.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1997, 119, 10935. DOI
Keywords: Diol -> Ketal • Alkyl-OH -> Aldehyde • O-H -> O-SiPh2tBu • Ketal -> Diol • Pfitzner-Moffat • Alkyl-OH -> Aldehyde-α-OR • Pfitzner-Moffat • Propargyl-OH -> Ynone • O-H -> O-SiEt3 • Lactol -> Lactone • O-SiEt3 -> O-H • Alkyl-OH -> Aldehyde • O-H -> O-SiEt3 • CarboxEster(thio) -> Aldehyde • O-H -> O-SiEt3 • Li-Vinyl -> Mg-Vinyl • Allyl-OH -> Enone • O-SiEt3 -> O-H • CarboxEster -> CarboxAcid • O-H -> O-SiEt3 • Alkyl-OH -> Ketone • O-SiEt3 -> O-H • O-SiPh2tBu -> O-H • B-Allyl-Ipc+Aldehyde • Corey-Fuchs • Fritsch-Buttenberg-Wiechell • Yamaguchi lactonization • Macrolactonization • Lactone-15+ • 2,3-Sigmatropic Anionic • CarboxEster(thio) enolate+Aldehyde • Aldol-Li -> Aldol • Li/Br -> Li-Vinyl • CarboxEster enolate+Lactone • EC-Aldehyde/CarboxEster+Mg-R • Hydrogenation-Lindlar • Mg-Alkyl+Ynone • Li-Alkynyl+Aldehyde • Mg-Allyl+Epoxide • Alkyne Hydrozirconation • Li/Sn -> Li-Ether • Hydrogenolysis Acyl-SR • Mg-Vinyl+Aldehyde • Ozonolysis • Diol -> Epoxide •
Reagents: BH3 • Et2C(OMe)2 • CrO3Cl·PyH (PCC) • Allyl-B(Ipc)2 • H2O2, NaOH • SiPh2tBu-Cl • Me2S • Citric acid • DMSO, carbodiimide • Alkynyl-Li • DMSO, carbodiimide • MeMgBr • Carbonate, calcium • KH • TsOH • HSiEt3 • Ag2CO3 • CH2=C(OLi)(OR) • Citric acid • Dess-Martin • LiNiPr2 • HSiEt3 • HSiEt3 • Pd/C • Ph3P=CBr2 • BuLi(n) • ZrCp2ClH • Acetic acid • NaH • Crotyl-MgX • HSiEt3 • BuLi(tert) • Dess-Martin • Camphor sulfonic acid • BH(OAc)3-Me4N+ • Hydroxide, lithium • Benzoyl chloride, 2,4,6-trichloro • HSiEt3 • Dess-Martin • HF • Fluoride, Bu4N+ • Carbodiimide • Carbodiimide • Carbodiimide • SnBu3-CH2-I • MgBr2 • BuLi(n) • NBS • 18-cr-6 •

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