TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE
TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE
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DOI：
10.1021/jo00068a045
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发表时间：
1993-07-30
影响因子：
3.6
通讯作者：
OGAWA, S
中科院分区：
文献类型：
--
作者：
CHIDA, N;OHTSUKA, M;OGAWA, S
以D-葡萄糖为起始原料，立体选择性全合成了抗有丝分裂生物碱（+）-力可利西定（1）及其2-差向异构体（30）。在这个合成中的关键步骤是（i）的Ferrier重排的催化版本的光学活性取代的环己烯酮（的C-环的力可利西定）的制备和（ii）钯催化的分子内Heck型，反应的菲酮骨架的建设。初步的生物活性测定表明，在2-位的立体化学的力可西定起着重要的作用，在其细胞毒活性。
Stereoselective total synthesis of antimitotic alkaloid (+)-lycoricidine (1) and its 2-epimer (30) was accomplished starting from D-glucose. The key steps in this synthesis are (i) a catalytic version of the Ferrier rearrangement for the preparation of the optically active substituted cyclohexenone (the C-ring of lycoricidine) and (ii) a Pd-catalyzed intramolecular Heck-typE, reaction for construction of the phenanthridone skeleton. A preliminary biological assay revealed that the stereochemistry at the 2-position of lycoricidine plays an important role in its cytotoxic activity.