This paper is dedicated to Dr. 0. E. (Ted) Edwards TAKEHIRO SANO, JUN TODA, NOBUTERU MAEHARA, and YOSHISUKE TSUDA. Can. J. Chem. 65,94 (1987).Total synthesis of dl-coccuvinine l a and dl-coccolinine 2a, "abnormal-type" erythrinan alkaloids lacking the C(16) 0-function at the aromatic ring, was effectively achieved by using the Diels-Alder reaction of dioxopyrroline. Isoquinolinopyrrolinedione 6a, a key dienophile, was synthesized via the tetrahydroisoquinoline 5a, which was prepared by BischlerNapieralski cyclization of the arnide 4 a at the unactivated position. The Diels-Alder adduct 7 a of 1,3-bis(trimethylsily1oxy)-butadiene with 6 a with converted stereoselectively into these alkaloids in short steps.