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. Author manuscript; available in PMC: 2009 Sep 10.

Published in final edited form as: J Am Chem Soc. 2008 Aug 15;130(36):11970–11978. doi: 10.1021/ja804105m

Scheme 4 — Synthesis of Leukotriene B₄^a ^a Reaction conditions: a) NaH, TBDMSCl, 62%; b) Red-Al, 88%; c) (COCl)₂, DMSO, Et₃N, 84%; d) borane 18, then NaOH, H₂O₂, 67%; e) TBDPSCl, imidazole, DMAP; f) CSA, MeOH, 81% over 2 steps; g) 2, In(OTf)₃, CSA, 92%; h) [(Ph₃PCH₂Br]Br, t-BuOK, 65%; i) n-BuLi, OHC(CH₂)₃COOCH₃, 27%, 67%brsm; j) TBDPSCl, imidazole, DMAP; k) H₂, Lindlar, quinoline, 92%; l) TBAF, 87%.