Stereoselective routes to the C10-C19 fragment of FK-506

Article abstract of DOI:10.1021/jo00296a041

D-Galactose was used as a starting material to reach the titled system. The key elements of one of the syntheses involved directed homogeneous hydrogenation and diastereoselective lactonization reactions (see 26 → 6 and 6 → 7). In another synthetic route directed catalytic hydrogenation was used to fashion 34 where the end groups were already differentiated.