Calyciphylline D, a novel alkaloid with an unprecedented fused-pentacyclic skeleton from Daphniphyllum calycinum

Shizuka Saito; Takaaki Kubota; Eri Fukushi; Jun Kawabata; Huiping Zhang; Jun'ichi Kobayashi

doi:10.1021/ol0631455

Calyciphylline D, a novel alkaloid with an unprecedented fused-pentacyclic skeleton from Daphniphyllum calycinum

Org Lett. 2007 Mar 29;9(7):1207-9. doi: 10.1021/ol0631455. Epub 2007 Mar 6.

Authors

Shizuka Saito¹, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Huiping Zhang, Jun'ichi Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.

PMID: 17338533
DOI: 10.1021/ol0631455

Abstract

[structure: see text]. Calyciphylline D (1), a novel Daphniphyllum alkaloid with an unprecedented fused-pentacyclic skeleton containing a 8-azatricyclo[4.2.1.0.4,8]nonane ring system, has been isolated from the leaves of Daphniphyllum calycinum (Daphniphyllaceae), and the structure and relative stereochemistry were elucidated on the basis of spectroscopic data.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Aza Compounds / chemistry*
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / isolation & purification*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Plant Leaves / chemistry
Polycyclic Compounds / chemistry
Polycyclic Compounds / isolation & purification*
Saxifragaceae / chemistry*
Stereoisomerism

Substances

Alkaloids
Aza Compounds
Heterocyclic Compounds, 4 or More Rings
Polycyclic Compounds
calyciphylline D