Total synthesis of (–)-(3R,6S,9R)-decarestrictine C2

Enantioselective synthesis of the proposed structure of (−)-(3R,6S,9R)-decarestrictine C2 (4) has been accomplished using (2S,5S)-1,2,5,6-hexanetetrol (9) as a C2-symmetric chiral synthon, in which the diastereoselective aldol-type reaction of a tin(II) enolate of 3-acetyl-4(S)-isopropyl-1,3-thiazolidine-2-thione with the α,β-unsaturated aldehyde was used as a key step.