The etructures assigned earlier to pipoxlde and pipoxlde ohlorohydrin have been revised on the basis of 360 Liz PM2 spectral evidence and deooupllng experiments. In the aourse of chemical investigation of Piper species, i-5 we have examined four plants viz., P. attenuatum, P. aaleatum, P. hookeri a
Crystal and molecular structure of lycorine-chlorohydrin: Revision of the stereochemistry
β Scribed by Jun Toda; Takehiro Sano; Yoshisuke Tsuda; Miyuki Kaneda; Yoichi Iitaka
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- French
- Weight
- 128 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Action of POCls and HCl on 1-0-acetyllycorine gave, quantitatively, O-acetyllycorine-chlorohydrin, which was convertible, in good yield, to lycorene-a-oxide and so-called lycorine-cis-chlorohydrin.
The configuration of the latter compound was revised establishing as tram by a single crystal X-ray analysis.
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A stereoselective total synthesis of the proposed structure of kaitocephalin (1) was accomplished starting from L-proline and D-and L-serines. However, its 1 H NMR spectral data and retention time on HPLC were not identical with those of authentic natural kaitocephalin. The revised stereochemistry o