189013-33-0Relevant academic research and scientific papers
Total synthesis of (-)-balanol, all stereoisomers, their N-tosyl analogues, and fully protected ophiocordin: An easy route to hexahydroazepine cores from garner aldehydes
Srivastava, Ajay Kumar,Panda, Gautam
experimental part, p. 4675 - 4688 (2009/05/07)
Total syntheses of (-)-balanol and all of its stereoisomers starting from easily available Garner aldehydes are described. Diastereoselective Grignard reactions on Garner aldehydes and ring-closing metatheses are the key steps for the construction of hexahydroazepine subunits. The benzophenone subunits were constructed through coupling of suitably functionalized aromatic aldehyde and bromo components. The synthetic route constitutes a convenient and scalable reaction sequence to generate all of the stereoisomers of balanol. The methodology is explored further for the synthesis of N-tosyl analogues of balanol and of fully protected ophiocordin.
Total synthesis of balanol, part 2. Completion of the synthesis and investigation of the structure and reactivity of two key heterocyclic intermediates
Tanner, David,Tedenborg, Lars,Almario, Antonio,Pettersson, Ingrid,Csoeregh, Ingeborg,Kelly, Nicholas M.,Andersson, Pher G.,Hoegberg, Thomas
, p. 4857 - 4868 (2007/10/03)
A convergent enantioselective total synthesis of the natural product (-)-balanol (1) is described. In addition to benzophenone fragment 8, key intermediates are chiral bicyclic aziridine 3 and the corresponding epoxide 4, both of which undergo highly regi
