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Total synthesis of Spongistatin 1 - (partial, Part 1) (Smith):
Reference: Smith, A. B., III; Zhuang, L.; Brook, C. S.; Boldi, A. M.; McBriar, M. D.; Moser, W. H.; Murase, N.; Nakayama, K.; Verhoest, P. R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667, DOI-1 DOI-2 DOI-3 (Part 2)
Keywords: O-H → O-Boc • Li/H → Li-Sulfone • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • B-Allyl-Ipc+Aldehyde • Li-Dithiane+Epoxide • Iodolactonization • B-Allyl-Ipc+Aldehyde • Julia-Type II • Li-Dithiane+Aldehyde • Aldehyde+Li-Sulfide • Iodohydrin → Epoxide • O-SiPh2tBu → O-H • O-H → O-C(O)R • O-H → O-Bn • Sharpless epoxidation • Epoxide → Diol • Oxymercuration Alkene • Ether-6 • Alkyl-Hg → Alkyl-OH • O-C(O)R → O-H • Diol-1,3 → Ketal • Alkyl-OH → Aldehyde • Aldehyde epimerization • O-H → O-Piv • O-Bn → O-H • O-H → O-SiPh2tBu • O-Piv → O-H • Alkyl-OH → Alkyl-I • Li-Sulfone+Epoxide • O-H → O-SiMe2tBu • O-H → O-Bn • O-SiPh2tBu → O-H • Alkyl-OH → Alkyl-I • Alkyl-X → Alkyl-Phosphonium • O-H → O-SiMe2tBu • Ketal → 1,3-Diol • Ketal(thio) → Ketone • O-H → O-SiMe2tBu • Ketone → Ketal •
Reagents: Crotyl-B(Ipc)2 • BF3·OEt2 • H2O2, NaOH • Boc2O • IBr • Carbonate, potassium • Epoxide • Crotyl-B(Ipc)2 • BF3·OEt2 • H2O2, NaOH • BuLi(n) • Me2C(OMe)2 • BuLi(n) • LiCHR-Sulfonyl • BuLi(n) • Chiral auxiliary-Boronate • Chiral auxiliary-Boronate • NaN(SiMe3)2 • Alkyl-MgX • Benzyl-X • Fluoride, R4N+ • Ti(OiPr)4 • Hydroperoxide, tbutyl • Ti(OiPr)4 • Hg(OAc)2 • Acetic anhydride, NEt3 • O2 • BH4-Na+ • Hydroxide, sodium • Acetone (solvent) • TsOH • DMSO (solvent) • NEt3 • SiMe2tBu-OTf • Acetic acid, trifluoro • Hg(ClO4)2 • Piv-Cl • SiMe2tBu-Cl • H2, Pd • SiPh2tBu-Cl • AlHiBu2 • Sulfonyl chloride, methane • LiCH2-Sulfonyl • HMPA (solvent) • NaH • Iodide, R4N+ • Lutidine • Hydroxide, sodium • Sulfonyl chloride, methane • Carbonate, calcium •

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