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Total synthesis of Spongistatin 1 - (Part 1):
Reference: Smith, A. B.; et al Tetrahedron Lett. 1997, 38, 8667, 8671, 8675. DOI, DOI, DOI, Part 2
Keywords: O-H → O-Boc • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Li-Dithiane+Epoxide • Iodolactonization • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Julia-Type II • Cu-Vinyl+Epoxide • Epoxide+Cu-R • Li-Dithiane+Epoxide •
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 • LiCH2-Sulfonyl • HMPA (solvent) • SiMe2tBu-OTf • BuLi(n), HMPA • LiCHR-Sulfonyl • BuLi(n) • BuLi(tert) • Epoxide • Epoxide • Epoxide • CuI • Chiral auxiliary-Boronate • Chiral auxiliary-Boronate • NaN(SiMe3)2

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