Synthesis of [5]helicenes with a substituent exclusively on the interior side of the helix by metal-catalyzed cycloisomerization

Kosuke Yamamoto; Mieko Okazumi; Hiroshi Suemune; Kazuteru Usui

doi:10.1021/ol400332j

Synthesis of [5]helicenes with a substituent exclusively on the interior side of the helix by metal-catalyzed cycloisomerization

Org Lett. 2013 Apr 19;15(8):1806-9. doi: 10.1021/ol400332j. Epub 2013 Mar 29.

Authors

Kosuke Yamamoto¹, Mieko Okazumi, Hiroshi Suemune, Kazuteru Usui

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka, 812-8582, Japan.

PMID: 23541218
DOI: 10.1021/ol400332j

Abstract

[5]Helicenes with a substituent exclusively oriented toward the interior curvature of the helix are synthesized by metal-catalyzed cycloisomerization. In addition, novel azulene-fused helicenes have been found through cycloisomerization studies. These [5]helicenes shows a high enough configurationally stability to allow resolution by HPLC on a chiral stationary phase.

Publication types

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

MeSH terms

Catalysis
Chromatography, High Pressure Liquid
Models, Molecular
Molecular Conformation
Molecular Structure
Platinum Compounds / chemistry*
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry
Stereoisomerism

Substances

Platinum Compounds
Polycyclic Compounds
helicenes
platinum chloride