191352-08-6Relevant academic research and scientific papers
Total synthesis of the piperidinol alkaloid (-)-(2R,3R,6S)-cassine
Oetting, Joerg,Holzkamp, Jens,Meyer, Hartmut H.,Pahl, Axel
, p. 477 - 484 (2007/10/03)
A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral β-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine.
Diastereoselective and convergent synthesis of both 11′-epimers of (-)-(2R,3R,6S)-carnavaline
Pahl, Axel,Oetting, Joerg,Holzkamp, Jens,Meyer, Hartmut H.
, p. 7255 - 7266 (2007/10/03)
Enantio- and diastereoselective syntheses of both 11′-epimers of (-)-carnavaline 1 have been achieved. Since the configuration of the remote chiral centre in the C-12 side chain of naturally occurring (-)-carnavaline had been unknown and spectroscopic data were not conclusive, an assignment of the 11′S-epimer to the natural product by comparison of the melting points is discussed and complete spectroscopic data are given.
