Bildung 12- bis 40-gliedriger Oligolide aus enantiomerenreinen 3-Hydroxybuttersäure-Derivaten – Bausteine für eine 21- und eine 31-Helix

Abstract

Trimeric, tetrameric, and pentameric oligolides are formed preferentially from (S)-?-butyrolactone, or from methyl (R)-3-hydroxybutanoate, upon prolonged treatment with catalytic amounts of tetraoxadistannacyclodecane (Shanzer's macrolactonization catalyst) in refluxing xylene. The crystal structure of the tetramer is described. Substructures of the larger folded oligolides are used for the construction of a left-handed 21-helix, as found in the biopolymer PHB, and a heretofore unknown right-handed 31-helix.