An efficient synthesis strategy to the core structure of 6-5-6-5-6-membered epipolythiodiketopiperazines.
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.
Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich , CH-8093 Zürich, Switzerland.
Hannes F
HF
Zipfel
Erick M
EM
Carreira
D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D010879:Piperazines; C555444:epipolythiodiketopiperazine