Scheme 9.

Biomimetic Total Synthesis of Polycitrin A (60)^a

^a Reagents and conditions: (i) (1) THF, n-BuLi, −78 °C, (2) 0.5 equiv, I₂, −78 to 25 °C, (3) NH₃, TiCl₄, 72%; (ii) NaOCl,95%; (iii) NaHSO₃; (iv) (1) KOH, (2) HCl, 75%; (v) BBr₃, 78%; (vi) Br₂, AcOH,83%; (vii) tyramine, diisopropylethylamine, PhOH (melt), 160 °C, 78%. (Reprinted with permission from ref 57. Copyright 1995 Elsevier B.V.)