Total synthesis of Dichrocephone B:
| Reference: | Schmiedel, V. M.; Hong, Y. J.; Lentz, D.; Tantillo, D. J.; Christman, M. Angew. Chem. Int. Ed. 2018, 570, 2419-2422 DOI |
| Reactions: | Wittig catalytic (asym) • Wittig-ketomethyl → Enone • Cyclopentenone • Bicyclo(330) • Alkyne → Alkynyl-Br • Alkyne → Ketone • ConjAdd Cu-Vinyl • Cu-Vinyl+Enone • RCM → Ring-C • Cyclopentene • Propellane(333) • Ketone → Alkyl-OH • CompRed-Ketone/Ketone+M-H • Mg-Alkyl+Ketone • Hydrogenation Alkene • Alkyl-OH → Ketone • Mannich • Cyclopropanation S-ylide • Sulfonium ylide+Enone • Corey-Chaykowsky • Spiro(42) • Enone epoxidation, nucleophilic • Epoxide reduction • Diol-1,2 → Ketone-α-OR • Dehydration → Ene • Alkene hydration • Ether-4 • Bicyclo(320)-oxa • |
| Reagents: | NBS • AgNO3 • AuNTf2 • HSiPhH2 • Vinyl-Cu • BH(sBu3)-K+ • Me-MgCl • H2, Pd • CrO3Cl·PyH (PCC) • Acetic anhydride • CH2(NMe2)2 • NaH • Me2S(O)=CH2 • H2O2 • AlH4-Li+ • H2, Pt • DMSO, Py·SO3 (Parikh-Doering) • NEt3 • Formic acid • HSiPhH2 • O2 • BF3·OEt2 • Acetate, sodium • Peracetic acid • |