Total Synthesis of (+)-Lycoricidine and Its 2-Epimer from d-Glucose

Noritaka Chida, Masami Ohtsuka, Seiichiro Ogawa

研究成果: Article査読

81 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)4441-4447
ページ数7
ジャーナルJournal of Organic Chemistry
58
16
DOI
出版ステータスPublished - 1993

ASJC Scopus subject areas

  • 有機化学

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