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An Efficient Synthesis Strategy to the Core Structure of 6–5–6–5–6-Membered Epipoly­thiodiketo­pipera­zines

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journal contribution
posted on 06.06.2014, 00:00 by Hannes F. Zipfel, Erick M. Carreira
A concise route to the core structure 1 of 6–5–6–5–6-membered epipoly­thiodiketo­pipera­zines is described. The strategy relies on construction of the pyrrolines by double nucleophilic opening of a bis(oxabicyclo­[2.2.1]­heptene) 2, obtained after bidirectional condensation of N,N′-diacetyl­diketo­pipera­zine (4) with aldehyde 3.