Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus.

Abstract

We report a concise synthesis of A-factor, the prototypical γ-butyrolactone signalling compound of Streptomyces bacteria. In analogy to enzymatic reactions in A-factor biosynthesis, our synthesis features a tandem esterification-Knoevenagel condensation yielding a 2-acyl butenolide and a surprising, chemoselective conjugate reduction of this α,β-unsaturated… (More)
DOI: 10.1039/c2ob06653j

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@article{Morin2012ReplicationOB, title={Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus.}, author={Jesse B. Morin and Katherine L Adams and Jason K Sello}, journal={Organic & biomolecular chemistry}, year={2012}, volume={10 8}, pages={1517-20} }