The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether†
James E. Robinson,Margaret A. Brimble
Chemical Communications Pub Date : 01/26/2005 00:00:00 , DOI:10.1039/B418106A
Abstract

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).

Graphical abstract: The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether