Enantioselective synthesis of hematoporphyrin stereoisomers

✍ Scribed by Dirk Kusch; Franz-Peter Montforts

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 193 KB
• Volume: 6
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/0957-4166(95)00091-3

✦ Synopsis

The reduction of 3,8-diacetyl porphyrin I with borane-methyl sulfide complex, BMS, as stoichiometric reductant and rnethyloxazaborolidine 2 and ent-2 as catalysts allows the enantioselective preparation of hematoporphyrin IX dimethyl ester stereoisomers.

Hematoporphyrin was first obtained by THUDICHUM in 1867 by acid hydrolysis of the red blood pigment heme 1. Since the hydrolysis is non-stereoselective, loss of the central iron ion and hydration of the