Highly efficient synthesis of novel methyl 132-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction

Jiazhu Li; Yang Liu; Xi-Sen Xu; Yan-Long Li; Shan-Guo Zhang; Il Yoon; Young Key Shim; Jin-Jun Wang; Jun-Gang Yin

doi:10.1039/C4OB02491E

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Highly efficient synthesis of novel methyl 13²-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction†

Jiazhu Li,^a Yang Liu,^a Xi-Sen Xu,^a Yan-Long Li,^a Shan-Guo Zhang,^a Il Yoon,^b Young Key Shim,^b Jin-Jun Wang*^a and Jun-Gang Yin*^c

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, Yantai University, Yantai, China
E-mail: wjj1955@163.com

^b PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae, Korea

^c College of Life Sciences, Yantai University, Yantai, China
E-mail: jungangyin@163.com

Abstract

Treatment of methyl mesopyropheophorbide a with formaldehyde under basic conditions gave a novel 13²-methylene derivative in 85% yield; under acidic conditions, the corresponding 20-hydroxymethyl derivative was obtained in 65% yield. The high reactivity of the enone structural motif existed in the former product provides a unique way to construct some novel chlorophyll a derivatives for various applications. Stereoselective Michael reaction of this compound is studied and discussed.

Download options Please wait...

Supplementary files

Supplementary information PDF (1968K)

Article information

DOI: https://doi.org/10.1039/C4OB02491E
Article type: Communication
Submitted: 27 Nov 2014
Accepted: 23 Dec 2014
First published: 23 Dec 2014

Download Citation

Org. Biomol. Chem., 2015,13, 1992-1995

Permissions

Request permissions

Highly efficient synthesis of novel methyl 13²-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction

J. Li, Y. Liu, X. Xu, Y. Li, S. Zhang, I. Yoon, Y. K. Shim, J. Wang and J. Yin, Org. Biomol. Chem., 2015, 13, 1992 DOI: 10.1039/C4OB02491E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry