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Total synthesis of Leucotriene A4 Methyl Ester:
Reference: Baker, S. R.; Clissoid, D. W.; McKillop, A. Tetrahedron Lett. 1988, 29, 991. DOI
Keywords: O-H → O-SO2R • Acetal → Diol • Wittig-alkyl → Ene-trans • Wittig-allyl → Diene • CompE+-Aldehyde/CarboxEster+Wittig • Wittig-alkyl → Ene-cis • Hydrogenation alkene • Diol-1,2 → Epoxide • Alkyl-OH → Aldehyde •
Reagents: PPh3=CH-Alkyl • BuLi(n) • Diazomethane • Sulfonyl chloride, methane, NEt3 • HCl, MeOH • PPh3=CH-Vinyl • PPh3=CH-Alkyl • BuLi(n) • Carbonate, potassium • CrO3·Py2 (Collins) • DMSO (solvent) •

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