Enantioselective syntheses and configuration assignments of gamma-chiral butenolides from Plagiomnium undulatum: butenolide synthesis from tetronic acids.
Both enantiomers of the gamma-chiral alpha,beta-dimethylated butyrolactones nat-1 and nat-2 from the moss Plagiomnium undulatum were synthesized stereoselectively through butenolides and tetronic acids, respectively. The configuration of the natural products was determined by GLC comparisons with mono(3-O-acetyl-6-O-tert-butyldimethylsilyl-2-O-methyl)hexakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin as a stationary phase.
Kapferer
Tobias
T
Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Albertstrasse 21, 79104 Freiburg, Germany.
Brückner
Reinhard
R
Herzig
Axel
A
König
Wilfried A
WA
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D019068:Bryopsida / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013997:Time Factors
D005663:Furans; D007783:Lactones; C004511:butenolide; C003422:tetronic acid; D015107:4-Butyrolactone