84-68-4Relevant articles and documents
Bidirectional synthesis of the central amino acid of chloptosin
Hong, Wen-Xu,Chen, Ling-Jun,Zhong, Chun-Long,Yao, Zhu-Jun
, p. 4919 - 4922 (2007/10/03)
(Chemical Equation Presented) An efficient total synthesis of (2S,2′S,3aR,3′aR,8aR,8′aR)-6,6′-dichloro-3a, 3′a-dihydroxy-1,1′,2,2′,3,3a,3′,3′a,8,8a,8′, 8′a-dodecahydro-5,5′-bipyr-rolo[2,3-b]indole-2,2′- dicarboxylic acid, the central amino acid component of chloptosin (1), is described. Starting from m-chloronitrobenzene, this C2-symmetrical amino acid was synthesized by using a 14-step route, in which a Zinin benzidine rearrangement, intramolecular Heck reaction, and selenocyclization and oxidative deselenation served as key steps. The absolute stereochemistry of the target was confirmed by X-ray single-crystal studies on a key intermediate (17).