Total synthesis of Spongistatin 2 - (Part 3) (Smith) New:
| Reference: | Smith, A. B., III; Doughty, V. A.; Lin, Q.; Zhuang, L; McBriar, M. D.; Boldi, A. M.; Moser, W. H.; Murase, N.; Nakayama, K.; Sobukawa, M.; Angew. Chem. Int. Ed. 2001, 40, 191. DOI-1 DOI-2 (Part 1) (Part 2) (Part 4) (Part 5) (Part 6) (Part 7) |
| Reactions: | Li/H → Li-Sulfone • Julia-Type II • O-Bn → O-H • Alkyl-OH → Ketone • Aldehyde → CarboxAcid • O-H → O-SiiPr3 • O-H → O-SiEt3 • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Alkyl-OH → Aldehyde • Ketal epimerization • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Li/H → Li-Sulfone • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • O-SiPh2tBu → O-H • O-SiMe2tBu → O-H • O-DMB → O-H • O-H → O-C(O)R • Spiroketal • |
| Reagents: | BuLi(n) • HMPA (solvent) • BuLi(n) • Alkyl-MgX • CH2I2 • Fluoride, R4N+ • SiMe2tBu-Cl • HClO4 • DDQ • Acetic anhydride, DMAP • SiEt3-OTf • HF·Py • Dess-Martin • Chlorite, sodium • Dess-Martin • SiiPr3-Cl • NEt3 • |