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(-)-Prelactone B

The prelactones 1-4 constitute an important class of highly functionalized chiral d -lactones isolated from various polyketide macrolide producing microorganisms. Prelactone B (2), ab-hydroxy d-lactone that contains a 2,3-trans-dialkylpyran ring system is a biologically important natural pyranone derivative isolated from bafilomycin-producing Streptomyces griseus (strain 2599 ana 18) by Zeek and Bindseil in 1993.  The discovery of these molecules supports the widely accepted hypothesis of step by step functionalization of growing polyketide chains in the biosynthesis of macrolides.

 

To date, four syntheses of prelactone B have been described. An efficient and flexible enantioselective synthesis of prelactone B is essential to provide further material for biological studies, along with access to novel analogues. The approach described here to (+)-prelactone B might give access to the other prelactones as well as to additional derivatives with potential relevance to biological studies.

  1. "A Short and Efficient Synthesis of (+)-Prelactone B". Dias, L. C.; Steil, L. J.; Vasconcelos, V. de A. Tetrahedron: Asymmetry 2003, 15, 147-150.

 

 

 

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