Abstract
Oteromycin is a HIV integrase inhibitor isolated from fungi MF5810 and MF5811, and has attracted a lot of attention for it's constructive features, decalin skeleton and alpha,beta-unsaturated-alpha-acyl-gamma-hydroxylactam moiety. In the initial stage of the total synthesis, the novel synthetic method of alpha,beta-unsaturated-alpha-acyl-gamma-hydroxylactam moiety was developed utilizing the catalytic acid-mediated dehydrogenation of alpha-acyl-gamma-hydroxylactam by DDQ. We succeeded in establishing the novel synthetic method, lanched synthesis of the decalin skeleton of Oteromycin. As a key step for the construction of the decalin skeleton, an intramolecular Diels-Alder (IMDA) reaction was adopted. The synthesis of the decalin equipped with all stereogenic centers has been achieved, starting from commercially available (+)-citronellal.
