Maackia tashiroi

Consequently, the MacMillan group reported a novel SOMO a-arylation reaction to achieve the total synthesis of ( )-tashiromine (165), isolated from the Asian deciduous shmb, Maackia tashiroi [67]. Organocatalytic a-arylation reaction of the pyrrole amide 163 afforded the key intermediate-bicycle 164 (72% yield, 93% ee), which was converted into ( )-tashiromine (165) by LiAHt reduction and hydrogenation using catalytic RI1/AI2O3 in 37% yield for the three steps as shown in Scheme 17.28 [66b],... 

A similar protocol in the same acidic solvent was used for the synthesis of the indolizidine alkaloid tashiromine isolated from an Asian deciduous shrub Maackia tashiroi (Scheme 4.44) [89]. 

---