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. Author manuscript; available in PMC: 2016 Jun 30.

Published in final edited form as: Chem Rev. 2007 Dec 21;108(1):264–287. doi: 10.1021/cr078199m

Scheme 2 — Synthesis of Lamellarin D (35)^a

^a Reagents and conditions: (i) (1) 85, NaH, DMF, (2) PdCl₂(pph₃)₂, PPh₃, K₂CO₃; (ii) NBS, THF; (iii) 88, Pd(PPh₃)₄, Na₂CO₃, DMF; (iv) i-PrBr, K₂CO₃, DMF; (v) NBS, THF; (vi) 92, Pd(PPh₃)₄, K₃PO₄, DMF; (vii) DDQ, CHCl₃, MW; (viii) AlCl₃, CH₂Cl₂; (ix) NaH, THF. (Reprinted with permission from ref 32. Copyright 2005 American Chemical Society.)