Asymmetric synthesis of optically active decahydroisoquinolines useful in HIV-1 protease inhibitor synthesis

Article abstract of DOI:10.1016/0040-4020(95)00266-B

An efficient synthesis of amino acid ester 8 is described featuring an asymmetric aza-Diels-Alder reaction of diene 5 and chiral imine 6 which establishes the asymmetry at C-3. Hydrogenation of 7 provides 8 with the desired asymmetry at C-4a and C-8a.