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The synthesis of DITOX, both in racemic and enantioenriched forms, was accomplished via sulfur oxidation of 1,3-dithiane or 2-acyl-1,3-dithiane derivatives, using chiral oxaziridines for the asymmetric process. The conjugate addition reaction of the α-sulfinyl carbanion derived from DITOX, prepared by deprotonation using the mixture of bases NaHMDS/n-BuLi, to the bicyclic γ-lactam unit of C-10b substituted dihydropyrrolo[2,1-a]isoquinolones led diastereoselectively to the corresponding trans isomer.

DITOX derived α-sulfinyl carbanion as nucleophile in conjugate addition reactions to pyrrolo[2,1-a]isoquinolones