The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether.
The first enantioselective synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether has been carried out in a convergent fashion by heterocycle-activated Julia olefination of a spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment. The total synthesis of (+)-spirolaxine methyl ether establishes the absolute stereochemistry of the natural product to be (3R,2''R,5''R,7''R).
Robinson
James E
JE
Department of Chemistry, The University of Auckland, 23 Symonds St., Auckland, New Zealand.
Brimble
Margaret A
MA
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D016480:Helicobacter pylori / Q000187:drug effects; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D013141:Spiro Compounds; C517924:spirolaxine methyl ether