Highly efficient synthesis of novel methyl 132-methylene mesopyropheophorbide a and its stereoselective Michael addition reaction. Issue 7 (8th January 2015)

• Record Type: Journal Article
• Authors: Li, Jiazhu; Liu, Yang; Xu, Xi-Sen; Li, Yan-Long; Zhang, Shan-Guo; Yoon, Il; Shim, Young Key; Wang, Jin-Jun; Yin, Jun-Gang
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 7(2015)
• Page Start: 1992
• Page End: 1995
• Publication Date: 2015-01-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02491e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : pH-Dependent regioselective condensation of methyl mesopyropheophorbide a with HCHO is studied and stereoselective Michael reaction of the 13 2 -methylene product is also discussed. Abstract : Treatment of methyl mesopyropheophorbide a with formaldehyde under basic conditions gave a novel 13 2 -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.