期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 2, 页码 869-878出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02719
关键词
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资金
- RGC-CRF [C4030-14G]
- UGC-AoE of HKSAR [AoE/P-03/08]
- Faculty of Science, CUHK [4053267]
The synthesis of enantiomerically pure, configurationally stable fenestrindane-based polyaromatic compounds with saddle-like structures is reported. Seven racemic fenestrane synthetic precursors were first screened by chiral HPLC for resolvability into enantiomers. Among the three resolvable precursors, a tribenzofenestrene derivative was resolved on a semipreparative scale, and the absolute configuration of the more slowly eluting enantiomer was established by X-ray crystallography. The enantiopure tribenzofenestrenes were then separately converted, in six steps, to the saddle-shaped fenestrindane derivatives in optically pure form. The two enantiomeric pairs of saddles were characterized by H-1 and C-13 NMR spectroscopy, mass spectrometry, and circular dichroism spectroscopy. All new compounds reported herein represent the first enantiopure non-natural carbocyclic fenestranes isolated to date.
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