Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment.
cis-Reticulatacin-10-ones A and B were synthesised as a predefined mixture of diastereoisomers (dr ∼ 1 : 9) in nine steps from the acid chloride 8, and without the use of hydroxyl protecting groups. Comparison of the chiral HPLC chromatogram of the synthetic sample with that of the natural product isolated from the roots of the tropical fruit tree Annona muricata L. showed the natural product to be a mixture of A and B diastereoisomers (dr ∼ 1 : 1).
Abdel Ghani
Sherif B
SB
Plant Protection Department, Faculty of Agriculture, Ain Shams University, Hadayek Shoubra 11241, Cairo, Egypt.
Brown
Lynda J
LJ
Figadère
Bruno
B
Brown
Richard C D
RC
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D031041:Annona / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D005663:Furans; D007783:Lactones; C545822:reticulatacin; D015107:4-Butyrolactone