Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes.
A highly stereoselective total synthesis of (+)-asimicin (1) is reported. The synthesis features two chelate-controlled [3 + 2] annulation reactions-one of which (e.g., 2 + 3) constitutes a key, convergent fragment assembly step-that establish all of the stereochemistry of the bis-tetrahydrofuran unit of the natural product.
Tinsley
Jennifer M
JM
Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA.
Roush
William R
WR
D005663:Furans / Q000138:chemical synthesis*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D012821:Silanes; C061022:bullatacin