Stereoselective synthesis -: meso compounds:: Stepchildren or favored children of stereoselective synthesis?

After more than a quarter of a century of development, the methodology of stereoselective synthesis appears to be fully matured. In line with this, the potential that meso compounds offer in stereoselective synthesis is clearly recognized. The use of meso compounds in synthesis is, however, in no way commensurate with this potential, because, ironically, the synthesis of meso compounds in the first place is a problem of stereoselective synthesis. Present-day methodology does not provide many useful solutions to this problem. This Review therefore addresses the strategies available for the synthesis of more elaborate meso compounds whose stereogenic centers have a distance > 1,4 between them. meso Compounds with more than four stereogenic centers are also considered. The criteria used in choosing from several strategies in the synthesis of such compounds are discussed.