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Beilstein J. Org. Chem. 2008, 4, No. 8, doi:10.1186/1860-5397-4-8
Graphical Abstract
Scheme 1: Retrosynthesis for tashiromine.
Scheme 2: Stereoselective construction of the indolizidine core 2.
Scheme 3: Completion of the total synthesis of tashiromine 1.
Figure 1: Rationale for stereoselective assembly of the indolizidine core using chiral allylsilanes.
Scheme 4: Asymmetric synthesis of chiral (alkoxy)allylsilanes.
Scheme 5: Attempted cross-metathesis of (alkoxy)allylsilanes.
Scheme 6: Competing isomerisation processes in attempted cross-metathesis of (hydroxy)allylsilane 12.