A short and practical synthesis of two Hagen's gland lactones.
A seven-step total synthesis of Hagen's gland lactones 1 and 2 starting from 1,2-O-isopropylidene-alpha-D-xylofuranose 3 is reported. The success of this short and practical synthesis depends on the use of two key reactions: a stereoselective nucleophilic substitution at the anomeric position of 5 and 6, which allowed the construction of the gamma-lactone ring, and an alkyl substitution reaction on tosylated compound 4, which permitted the carbon chain elongation of the tetrahydrofuran ring appendage at C-6.
Paz-Morales
Evelyn
E
Centro de Investigación de la Facultad de Ciencias Químicas, BUAP. 14 Sur Esq. San Claudio, San Manuel, Puebla, Mexico.
Melendres
Ruth
R
Sartillo-Piscil
Fernando
F
D000818:Animals; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry; D010572:Pest Control, Biological; D013237:Stereoisomerism; D013379:Substrate Specificity; D014863:Wasps / Q000737:chemistry*
C516586:1,2-isopropylidene-alpha-D-xylofuranose; D007783:Lactones; D009005:Monosaccharides