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Full Paper
Synthesis and Structure of Macrolactams of 3α-Aminodeoxycholanic Acid
Article first published online: 26 AUG 2005
DOI: 10.1002/ejoc.200500408
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Feigel, M., Ladberg, R., Winter, M., Bläser, D. and Boese, R. (2006), Synthesis and Structure of Macrolactams of 3α-Aminodeoxycholanic Acid. Eur. J. Org. Chem., 2006: 371–377. doi: 10.1002/ejoc.200500408
Publication History
- Issue published online: 2 JAN 2006
- Article first published online: 26 AUG 2005
- Manuscript Received: 7 JUN 2005
Keywords:
- Macrocycles;
- Steroids;
- Lactams;
- Conformation analysis
Abstract
The macrolactams cyclo(3α-aminodeoxycholic amide)2 (1) and cyclo(3α-aminodeoxycholic amide)3 (2) were prepared in high yields (1: 32 %; 2: 41 %) from the pentafluorophenyl esters of the linear precursors. The solid-state structures of both macrocycles were determined by X-ray diffraction. Compound 1 forms a cleft of C2 symmetry which holds two methanol and two water molecules fixed by hydrogen bonds. The crystals of compound 2 contain two slightly different macrolactam rings of 7–8 Å diameter. The polar α-surface of the deoxycholanic parts and the amide NH groups are oriented into the center of the rings. The cavity formed by the ring system and the void volume between the macrocycles is filled by disordered solvent molecules. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)