Scheme 10.

Total Synthesis of Polycitrin B (61)^a

^a Reagents and conditions: (i) Br₂,FeBr₂, 80%; (ii) MeONa, MeOH, (CO₂Me)₂, 99%; (iii) (CF₃SO₂)₂O, iPr₂NEt,CH₂Cl₂, 84%; (iv) 169, Pd₂dba₃, Ph₃P,DMF, 81%; (v) Me₃SiCl, NaI, MeCN, 92%; (vi) NaOH, H₂O, MeOH, 77%; (vii) Br₂,AcOH, 89%; (viii) tyramine, iPr₂NEt, phenol, molecular sieves, 140 °C. (Reprinted with permission from ref 60. Copyright 2000 Elsevier B.V.)