Total synthesis of (+)-lycoricidine and its 2-epimer from D-glucose

Noritaka Chida, Masami Ohtsuka, Seiichiro Ogawa

Research output: Contribution to journalArticle

78 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4441-4447
Number of pages7
JournalJournal of Organic Chemistry
Volume58
Issue number16
Publication statusPublished - 1993

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Glucose
Antimitotic Agents
Stereochemistry
Alkaloids
Assays
lycoricidine
phenanthridone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of (+)-lycoricidine and its 2-epimer from D-glucose. / Chida, Noritaka; Ohtsuka, Masami; Ogawa, Seiichiro.

In: Journal of Organic Chemistry, Vol. 58, No. 16, 1993, p. 4441-4447.

Research output: Contribution to journalArticle

Chida, Noritaka ; Ohtsuka, Masami ; Ogawa, Seiichiro. / Total synthesis of (+)-lycoricidine and its 2-epimer from D-glucose. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 16. pp. 4441-4447.
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