Journal
CHEMICAL COMMUNICATIONS
Volume -, Issue 43, Pages 4506-4508Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b612757f
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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 H-1 and C-13 NMR data, optical rotations and HPLC retention times of the synthetic compounds (3S, 2S, 5S, 7S)-(1a) and (3S, 2S, 5R, 7S)-(2a) and the (3R)-diastereomers (3R, 2S, 5S, 7S)-(1b) and (3R, 2S, 5R, 7S)-(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.
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