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. Author manuscript; available in PMC: 2008 Sep 11.
Published in final edited form as: J Org Chem. 2006 Jan 20;71(2):629–635. doi: 10.1021/jo052030w

Scheme 2. Synthesis of Long-Chain Alcohol 14.

Scheme 2

(a) LiNH(CH2)3NH2, t-BuOK/H2N(CH2)3NH2; (b) DHP, PPTS, CH2Cl2; (c) i. n-BuLi, THF, −78 °C to rt; ii. allyl bromide, CuI, THF, −78 °C; (d) i. 9-BBN, THF, −15 °C to rt; ii. 4-bromobenzophenone, Pd(PPh3)4, K3PO4, THF/DMF, reflux, 2 h; (e) PPTS (cat.), MeOH; (f) H2, Lindlar, MeOH.