Synthesis of the spiroacetal-containing anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014.
The first synthesis of the spiroacetal-containing anti-Helicobacter pylori agents ent-CJ-12,954 and ent-CJ-13,014 is reported based on the union of a heterocycle-activated spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment; comparison of the 1H and 13C NMR data, optical rotations and HPLC retention times of the synthetic compounds (3S,2"S,5"S,7"S)-(1a) and (3S,2"S,5"R,7"S)-(2a) and the (3R)-diastereomers (3R,2"S,5"S,7"S)-(1b) and (3R,2"S,5"R,7"S)- (2b) with the naturally occurring compounds established that the synthetic isomers (1a) and (2a) were in fact enantiomeric to the natural products CJ-12,954 and CJ-13,014.
Brimble
Margaret A
MA
Department of Chemistry, The University of Auckland, 23 Symonds St., Auckland, New Zealand. m.brimble@auckland.ac.nz
Bryant
Christina J
CJ
D000080:Acetals; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis; D016480:Helicobacter pylori; D013141:Spiro Compounds / Q000138:chemical synthesis
D000080:Acetals; D000900:Anti-Bacterial Agents; D001572:Benzofurans; C109706:CJ 12954; C109705:CJ 13014; D013141:Spiro Compounds