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. Author manuscript; available in PMC: 2008 Dec 27.
Published in final edited form as: J Am Chem Soc. 2006 Oct 11;128(40):13255–13260. doi: 10.1021/ja063860+

Scheme 6 a.

Scheme 6 a

a Reagents and conditions: (a) (MeHN)2CNMe2N3, CHCl3, 84% (2:1 E:Z); (b) PPh3, CH2Cl2, 75% (E), 58% (Z); (c) p-MeOC6H4CH2NCO, PhMe, 85 °C, 73% (E), 67% (Z); (d) 31, (ClCH2)2, 23 °C, 86% from E-34, 88% from Z-34; (e) TBAF, THF, 99%; (f) [Ir(cod)pyr(PCy3)]PF6, H2 (400 psi), CH2Cl2, 80%; (g) IBX, DMSO, CH3CN, 98%; (h) Me(CH2)7CH=PPh3, THF; (i) 10% Pd(OH)2/C, AcOH, H2 (1 atm), MeOH, 99%; (j) Me(CH2)7-CH=PPh3, THF, 50 °C, 72%; (k) (BocHN)2C=N(CH2)4OMs, Cs2CO3, DMF, 40 °C, 93%.