Total syntheses of dimmeric lycopodium alkaloid, complanadines A and B

Le Zhao, Eunsang Kwon, Yoshiji Takemoto, Masahiro Hirama, Chihiro Tsukano

研究成果: Article査読

抄録

Our total syntheses of lycopodium alkaloid lycodine (1), and its unsymmetric dimmer complanadines A (3) and B (4) were described. The bicyclo [3.3.1]nonane core structure of lycodine was constructed by regioselective Diels-Alder and intramolecular Mizoroki-Heck reactions. A late-stage coupling reaction of the lycodine units, pyridine N-oxide (+)-17 and aryl bromide (+)-16, through C-H arylation at the C1 position of (+)-17 provided the unsymmetric dimer structure. This strategy significantly simplified the construction of the dimeric architecture and functionalization. Total syntheses of complanadines A (3) and B (4) were achieved by adjusting the oxidation level of the bipyridine mono-N-oxide (+)-18. The diverse utility of this common intermediate (+)-18 suggests a possible biosynthetic pathway of complanadines in nature. Both enantiomers of lycodine (1) and complanadines A (3) and B (4) were prepared in sufficient quantities. The effect on neuron differentiation of PC-12 cells with human astrocytoma cells culture medium was evaluated.

本文言語English
ページ(範囲)135-144
ページ数10
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
77
2
DOI
出版ステータスPublished - 2019 1 1
外部発表はい

ASJC Scopus subject areas

  • Organic Chemistry

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