Synthesis of Both Top and Bottom Fragments of (-)-Talaromycin A through Enantiospecific and Diastereoselective Elaboration of Asymmetrized Tris(hydroxymethyl)methane

Article abstract of DOI:10.1021/jo00058a036

Asymmetrized tris(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported.Preparation of bottom half fragment 3 was achieved through a "protecting group-controlled" stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.