Synthesis 1990; 1990(1): 72-78
DOI: 10.1055/s-1990-26793
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Cyclic Guanidines; III1 Synthesis of Novel 8,13,15-Triazasteroids and Related Heterocycles

Franz Esser* , Karl-Heinz Pook, Alain Carpy
  • *Departments of Medicinal and Analytical Chemistry, Boehringer Ingelheim KG, D-6507 Ingelheim, Federal Republic of Germany
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17. September 2002 (online)

The Pictet-Spengler reaction is utilized for the generation of 8,13,15-triazasteroids and related multicyclic compounds. The constitution of 7a is elucidated by NMR- and X-ray analysis. A second route to the triazasteroid ring system by Bischler-Napieralski type cyclization is disclosed. Synthetic alternatives as well as the variability in size and nature of rings A, B, C and D of the steroid-like skeletons are demonstrated. Synthesis covers 14 new tetra- and pentacyclic compounds on the basis of 9 novel ring systems.