TOTAL SYNTHESIS OF (+)-LYCORICIDINE AND ITS 2-EPIMER FROM D-GLUCOSE

被引：81

作者：

CHIDA, N ^{[1
]}

OHTSUKA, M ^{[1
]}

OGAWA, S ^{[1
]}

机构：

[1] KEIO UNIV, FAC SCI & TECHNOL,DEPT APPL CHEM,3-14-1 HIYOSHI, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4441 / 4447

页数：7

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