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Total synthesis of Spongistatin 1 (partial):
Reference: Ley, S. V.; et al Org. Lett. 2003, 5, 4815, 4819. DOI
Keywords: Si-Alkynyl → H-Alkynyl • Diol-1,3 → Ketal • O-SiiPr3 → O-H • Alkyl-OH → Aldehyde • Propargyl-OH → Ynone • CarboxEster → Alkyl-OH • O-H → O-SiiPr3 • Li-Dithiane+Epoxide • Li-Alkynyl+Epoxide • Epoxide+Li-R • Li/H → Li-Alkynyl • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Mg-Alkynyl+Aldehyde • Ketone → Alkyl-OH • Ynone → Dithiane •
Reagents: Epoxide • Alkynyl-Li • BF3·THF • Epoxide • Vinyl-MgX • CuI • Fluoride, R4N+ • SiEt3-Cl • Alkynyl-MgX • BuLi(n) • Epoxide • I2, NaHCO3 • B(OMe)Et2 • Me2C(OMe)2 • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • Alkyl-MgX • Dess-Martin • Thiol, (CH2)3-SH • Thiol, (CH2)3-SH • AlH4-Li+ • SiiPr3-Cl • Propiolate • BH4-Na+ • Imidazole • Imidazole •

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