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Synthesis of (+)-Bullatacin via the Highly Diastereoselective [3+2] Annulation Reaction of a Racemic Aldehyde and a Nonracemic Allylsilane

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posted on 2005-09-15, 00:00 authored by Jennifer M. Tinsley, Eric Mertz, Pek Y. Chong, Robert-André F. Rarig, William R. Roush
A total synthesis of (+)-bullatacin has been accomplished via a diastereoselective [3+2] annulation reaction of the highly enantiomerically enriched allylsilane 3 and racemic aldehyde 4, which provides the key bis-tetrahydrofuran fragment 15 with ≥20:1 ds.