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Short Paper | Regular issue | Vol 85, No. 7, 2012, pp.1697-1710
Published online, 25th May, 2012
DOI: 10.3987/COM-12-12480
■ Determination of the Stereochemistry of C-2’ and C-3’ Positions of Taxine NA-1 (2’-Hydroxytaxine II) by the Asymmetric Synthesis of the Reductive Degradation Product of Its Side Chain Moiety

Wanxia Tang,* Hiroshi Minato, Mariko Ando, and Masayoshi Ando*

*Department of Pharmacy Engineering, College of Chemistry and Chemistry Engineering, Qiqihar University, 42 Wenhuadajie, Qiqihar, Heilongjian Shang, 161006, China

Abstract

The reductive degradation of taxine NA-1 (2'-hydroxytaxine II) with n-Bu4NBH4 gave taxinine A and (−)-3-dimethylamino-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 Sharpless 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, 3S) configuration. Thus, the absolute configuration of the side chain of taxine NA-1 (2'-hydroxytaxine II) at C-2' and C-3' positions was determined to be (2'R, 3'S).