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

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