Total synthesis of Spongistatin 2 - (Part 1) (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 2) (Part 3) (Part 4) (Part 5) (Part 6) (Part 7) |
| Reactions: | B-Allyl-Ipc+Aldehyde • Aldehyde+B-Allyl (asym) • Iodolactonization • Li-Dithiane+Epoxide • Wittig-carboxymethyl → EnoateEster • Sharpless epoxidation • O-H → O-Boc • Epoxide reduction • Diol-1,2 → Epoxide • EnoateEster → Allyl-OH • Iodohydrin → Epoxide • O-H → O-SiEt3 • Brook rearrangement • Mechanism • O-SiEt3 → O-H • Ketal → Diol-1,2 • Ketal(thio) → Ketone • Ketone → Ketal • Ether-6 • Alkyl-X → Alkyl-I • Li-Dithiane+Epoxide • O-H → O-SO2Ar • CompNu-O-H/O-H+RSO2X • Li/H → Li-Dithiane • |
| Reagents: | Allyl-B(Ipc)2 • H2O2, NaOH • Boc2O • IBr • BuLi(tert) • PPh3=C(Me)-CO2R • AlHiBu2 • Tartrate, diethyl • Ti(OiPr)4 • Hydroperoxide, tbutyl • BH4-Li+ • Ti(OiPr)4 • NaH • Imidazole • Carbonate, potassium • SiEt3-Cl • TMEDA • Epoxide • Acetic acid, trifluoro • TsCl • Me2C(OMe)2 • TsOH·Py • Hg(ClO4)2 • Lutidine • HClO4 • Iodide, lithium • Acetonitrile (solvent) • Epoxide • HOMe (react) • DMAP • |