Total synthesis of Spongistatin 1 (Partial, Part 2) (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 3) (Part 4) |
| Reactions: | O-H → O-CPh3 • Li/H → Li-Dithiane • Ketal(thio) → Ketone • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Si-Alkynyl → H-Alkynyl • O-H → O-SiEt3 • Li/H → Li-Dithiane • O-SiiPr3 → O-H • Ketal(thio) → Ketone • Ketone → C=CH2 • Petasis reagent • Li-Dithiane+Epoxide • Ketone → Alkyl-OH • Felkin-Anh Chelation • Diol-1,3 → Ketal • Alkyl-OH → Aldehyde • Aldehyde → Acetal(thio) • O-H → O-SiMe2tBu • Li-Dithiane+Epoxide • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Li-Dithiane+Epoxide • O-H → O-SiEt3 • Mg/H → Mg-Alkynyl • Li-Alkynyl+Aldehyde • Alkyl-OH → Ketone • |
| Reagents: | Ph3CCl • AlH4-Li+ • DMSO, (COCl)2 (Swern) • NEtiPr2 • SiMe2tBu-Cl • BuLi(n) • Epoxide • Alkynyl-SiR3 • Alkynyl-SiR3 • BF3·OEt2 • I2, NaHCO3 • SiEt3-Cl • TiCp2Me2 (Petasis) • Fluoride, R4N+ • SiEt3-Cl • BuLi(n) • Epoxide • I2, NaHCO3 • BH4-Na+ • Me2C(OMe)2 • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • NEt3 • TsOH·Py • Alkynyl-MgX • Dess-Martin • Thiol, (CH2)3-SH • BF3·OEt2 • Imidazole • Imidazole • Imidazole • |