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Note | Regular issue | Vol 65, No. 12, 2005, pp.2965-2971
Published online, 27th September, 2005
DOI: 10.3987/COM-05-10541
Formal Synthesis of (±)-Trachelanthamidine

Meng-Yang Chang,* Dong-Ciao Wu, and Nein-Chen Chang

*Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan, R.O.C.

Abstract

Base-induced coupling-cyclization stepwise [3+2] annulation of α-sulfonylacetamide with (Z)-2-bromoacrylate yielded the polysubstituted pyroglutamate with three contiguous chiral centers with trans-trans orientation in a one-pot synthesis. The pyrrolizidine skeleton was obtained via the ring-closing metathesis (RCM) method. This facile strategy was used to synthesize (±)-trachelanthamidine.