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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-1,2 → Ketal • Alkyl-OH → Aldehyde • O-H → O-SiPh2tBu • Ketal → Diol-1,2 • Alkyl-OH → Aldehyde-α-OR • Propargyl-OH → Ynone • O-H → O-SiEt3 • Lactol → Lactone • Lactone-6 • O-SiEt3 → O-H • Alkyl-OH → Aldehyde • O-H → O-SiEt3 • 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 • Aldol-B-Ipc • Corey-Fuchs • Fritsch-Buttenberg-Wiechell • Yamaguchi lactonization • Lactone-9+ • 2,3-Sigmatropic Anionic • CarboxEster(thio) enolate+Aldehyde • Aldol-Li → Aldol • Li/Br → Li-Vinyl • CarboxEster enolate+Lactone • CompE+-Aldehyde/CarboxEster+Mg-R • Hydrogenation Lindlar • Mg-Alkyl+Ketone • Ynone+Mg-R • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Mg-Allyl+Epoxide • Epoxide+Mg-R • Alkyne Hydrozirconation • Zr-Vinyl → X-Vinyl • Li/Sn → Li-Ether • Zr-Vinyl → X-Vinyl • Hydrogenolysis Acyl-SR • Mg-Vinyl+Aldehyde • Ozonolysis • Diol-1,2 → Epoxide •
Reagents: BH3 • Et2C(OMe)2 • CrO3Cl·PyH (PCC) • Allyl-B(Ipc)2 • H2O2, NaOH • SiPh2tBu-Cl • Me2S • Citric acid • DMSO, carbodiimide (Pfitzner–Moffatt) • Alkynyl-Li • DMSO, carbodiimide (Pfitzner–Moffatt) • MeMgBr • Carbonate, calcium • KH • TsOH • SiEt3-Cl • Ag2CO3 • CH2=C(OLi)(OR) • Citric acid • Dess-Martin • LiNiPr2 • SiEt3-OTf • HSiEt3, Pd • PPh3=CBr2 • BuLi(n) • Vinyl-Zr • Acetic acid • NaH • Crotyl-MgX • SiEt3-OTf • BuLi(tert) • Dess-Martin • Camphor sulfonic acid • BH(OAc)3-Me4N+ • Hydroxide, lithium • Benzoyl chloride, 2,4,6-trichloro • SiEt3-OTf • Dess-Martin • HF • Fluoride, R4N+ • Carbodiimide • Chiral auxiliary-Boronate • Carbodiimide • Carbodiimide • SnBu3-CH2-I • MgBr2 • BuLi(n) • Vinyl-Zr • NBS • 18-cr-6 •

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