title: 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 carbonyl compound using sodium cyanoborohydride.
authors.affiliation: Department of Chemistry, Brown University, Providence, RI, USA.
authors.forename: Jesse B
authors.initials: JB
authors.lastname: Morin
authors.forename: Katherine L
authors.initials: KL
authors.lastname: Adams
authors.forename: Jason K
authors.initials: JK
authors.lastname: Sello
mesh_terms: D015107:4-Butyrolactone / Q000096:biosynthesis / Q000737:chemistry*; D015394:Molecular Structure; D013305:Streptomyces griseus / Q000737:chemistry* / Q000378:metabolism
chemical_list: D015107:4-Butyrolactone