Total synthesis of Confertin:
| Reference: | Semmelhack, M. F.; Yamashita, A.; Tomesch, J. C.; Hirotsu, K. J. Am. Chem. Soc. 1978, 100, 5565-5567 DOI |
| Reactions: | Li/Br → Li-Vinyl • O-MOM → O-H • ConjAdd Cu-Vinyl • Cu-Vinyl+Enone • Enone+Cu-Vinyl • ConjAdd-Alkylation • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • ConjAdd M-SR • EnePhosphonate+Thiolate • EnoateEster+Thiolate • ConjAdd-Olefination • HWE → EnoateEster • Ni-Allyl+Aldehyde • Lactone-5 • Cycloheptane • Bicyclo(530) • Hydrogenation Alkene • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+DMSO • Sulfide → Sulfonium • Protecting group - Enoate • ConjAdd M-SR • Sulfide → Sulfonium • Dehydrosulfenylation → EnoateEster • |
| Reagents: | Vinyl-Li • BuLi(tert) • Bromoacetate • HMPA (solvent) • AlH4-Li+ • CrO3·Py2 (Collins) • Thiolate, propyl • EnePhosphonate • P(O)(OR)2CH2-C(O)OR' • Carbodiimide • MeOSO2F • Ni(cod)2 • Thiol, propyl • H2, Pd • MeOSO2F • Bicarbonate, sodium • |