Base-induced coupling-cyclization stepwise [3+2] annulation of £\-sulfonylacetamide with (Z)-2-bromoacrylate yielded the polysubsti- tuted pyroglutamate with three contiguous chiral centers with trans- trans orientation in a one-pot synthesis. The pyrrolizidine skeleton and the core of stenine were obtained via the ring-closing metathesis (RCM) method.This facile strategy was used to synthesize (¡Ó)-trachelantha- midine, (¡Ó)-supinidine and the core of stenine.