A modular and organocatalytic approach to gamma-butyrolactone autoregulators from Streptomycetes.
A general synthesis of optically active gamma-butyrolactone autoregulators is developed by a two-step sequence to assemble 2,3-trans-disubstituted butyrolactones in high yields and enantioselectivities; the scope of this reaction was elaborated by setting up a library of alkyl-substituted butyrolactones and the synthesis of the autoregulators IM-2 and VB-D.
Elsner
Petteri
P
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, Aarhus C, DK-8000, Denmark.
Jiang
Hao
H
Nielsen
Johanne B
JB
Pasi
Filippo
F
Jørgensen
Karl Anker
KA
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
C107543:IM 2 autoregulator; D015107:4-Butyrolactone