DETERMINATION OF THE STEREOCHEMISTRY OF C-2 %26apos; AND C-3 %26apos; POSITIONS OF TAXINE NA-1 (2 %26apos;-HYDROXYTAXINE II) BY THE ASYMMETRIC SYNTHESIS OF THE REDUCTIVE DEGRADATION PRODUCT OF ITS SIDE CHAIN MOIETY

作者：Tang Wanxia^*; Minato Hiroshi; Ando Mariko; Ando Masayoshi

来源：Heterocycles, 2012, 85(7): 1697-+.

DOI：10.3987/COM-12-12480

• Taxine NA-1
• Sharpless Asymmetric Epoxidation
• (2R,3S)-3-and (2S,3R)-3-Dimethylamino-3-phenylpropane-1,2-diols

The reductive degradation of taxine NA-1 (2%26apos;-hydroxytaxine II) with n-Bu4NBH4 gave taxinine A and (-)-3-dimethylarnino-3-phenylpropane-1,2-diol (1) in addition to 11,12-dihydrotaxinine A. The relative stereochemistry of (-)-1 was identical with syn-3-dimethylamino-3-phenylpropane-1,2-diol, (+/-)-1b, which was synthesized from cis-2,3-epoxy-3-phenylpropan-1-ol, (+/-)-7. The absolute configuration of (-)-1 was certified by comparison of the specific optical rotation and the spectroscopic data of (-)-1 with those of (+)-1b and (-)-1b, which were enantioselectively synthesized by Sharp less asymmetric epoxidation reaction of cis-cinnamyl alcohol (6), respectively. As the result, the relative and absolute configuration of (-)-1 was same with that of (-)-1b possessing (2R, 35) configuration. Thus, the absolute configuration of the side chain of taxine NA-1 (2%26apos;-hydroxytaxine II) at C-2%26apos; and C-3%26apos; positions was determined to be (2%26apos;R, 3%26apos;S).

• 出版日期2012-7-1
• 单位齐齐哈尔大学