Article

Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Organic Letters (impact factor: 5.86). 10/2005; 7(19):4245-8. DOI:10.1021/ol051719k pp.4245-8
Source: PubMed

ABSTRACT [reaction: see text] 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 > or = 20:1 ds.

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Keywords

diastereoselective [3+2] annulation reaction
 
enantiomerically enriched allylsilane 3
 
key bis-tetrahydrofuran fragment 15
 
total synthesis