Total synthesis of Spongistatin 2 - (Part 2) (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 3) (Part 4) (Part 5) (Part 6) (Part 7) |
| Reactions: | Cu-Vinyl+Epoxide • Epoxide+Cu-R • Li-Dithiane+Epoxide • O-H → O-SiMe2tBu • O-H → O-Piv • CompNu-O-H/O-H+RC(O)X • O-H → O-Boc • Iodohydrin → Epoxide • O-H → O-SiMe2tBu • Brook rearrangement • O-H → O-Me • O-SiMe2tBu → O-H • Ketal(thio) → Ketone • Alkyl-OH → Alkyl-I • O-Piv → O-H • Spiroketal • B-Allyl-Tartrate+Aldehyde • Aldehyde+B-Allyl (asym) • Aldehyde → Acetal(thio) • Ozonolysis • Ketal(thio) → Ketone • Ketone → Alkyl-OH • O-H → O-BOM • Reductive etherification • Diol-1,3 → Acetal • Alkyl-OH → Alkyl-I • Alkyl-X → Alkyl-SO2R • Li-Dithiane+Alkyl-X • Li/H → Li-Dithiane • |
| Reagents: | BuLi(tert) • Epoxide • Epoxide • Epoxide • Vinyl-Li • KN(SiMe3)2 • Boc2O • IBr • Carbonate, potassium • SiMe2tBu-Cl • TMEDA • NaH • MeI • 15-crown-5 • Hg(ClO4)2 • Carbonate, calcium • SiMe2tBu-Cl • Piv-Cl • HCl, MeOH • AlHiBu2 • HClO4 • I2 • Crotyl-B(tartrate) • Chiral auxiliary (boronate) • O3; PPh3 • Thiol, (CH2)3-SH • BF3·OEt2 • Benzaldehyde • TsOH·Py • BuLi(tert) • HMPA (solvent) • Hg(ClO4)2 • Carbonate, calcium • BH4-Na+ • Chloromethyl ether • AlHiBu2 • I2 • Sulfinate, benzene • DMF (solvent) • |