Total synthesis of Spongistatin 1 (Partial, Part 3) (Ley):
| Reference: | Gaunt, M. J.; Jessiman, A.S.; Orsini, P.; Tanner, H. R.; Hook, D. F.; Ley, S. V. Org. Lett. 2003, 5, 4819-4822. DOI (Part 1) (Part 2) (Part 4) |
| Reactions: | Ketal(thio) → Ketone • Li-R → Ce-R • O-PMB → O-H • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Alkyl-OH → Aldehyde • Pinnick oxidation • Aldehyde → CarboxAcid • Williamson esterification • CarboxAcid → CarboxEster • O-H → O-C(O)R • CompNu-O-H/O-H+RC(O)X • O-H → O-SiEt3 • CompNu-O-H/O-H+R3Si-X • Ynone → Dithiane • ConjAdd M-SR • Ynone+Thiolate • Ketone → Ketal(Spiro) • Ketal → Diol-1,3 • Ketone+Li-Alkyl • Ce-Me+Ketone • Alkyl-OH → Aldehyde • Aldol-BR2 → Aldol • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • Spiroketal • |
| Reagents: | NaOMe • HClO4 • SiMe2tBu-Cl • I2, NaHCO3 • Me-Li • CeCl3 • Acetic anhydride, DMAP • SiEt3-OTf • Dess-Martin • Chlorite, sodium • Allyl-Br • Carbonate, cesium • DDQ • HF·Py • Dess-Martin • Thiol, (CH2)3-SH • Lutidine • Imidazole • |