The first total synthesis of IPF2 alpha-III, a type III isoprostane is
described using a syn-anti-syn lactone 34 prepared from D-glucose and
a novel iodohydrin synthon 30. This is first synthesis of a represent
ative of type III isoprostane which is anticipated to be formed in viv
o from arachidonic acid by free-radical mechanism. This synthetic mate
rial will help elucidate the formation in vivo of type III isoprostane
s. (C) 1997 Elsevier Science Ltd.