Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 15, Pages 5839-5842Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0707885
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Funding
- NIGMS NIH HHS [GM 36238, R01 GM036238-20, R01 GM036238-19, R01 GM036238] Funding Source: Medline
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Two distinct approaches have been developed for the synthesis of chlorins bearing formyl groups: (1) reaction of an acetal-substituted 1-acyldipyrromethane with 2,3,5,6-tetrahydro-1,3,3-trimethyldipyrrin to give upon hydrolysis a 5-formylchlorin and (2) Pd-mediated coupling of a bromochlorin with a one-carbon synthon (hydroxymethyl tributyltin or CO) to give a 13-, 15-, or 3,13-formylchlorin. The zinc chlorins exhibit long-wavelength peak absorption maxima ranging from 626 to 667 nm, indicating the wavelength tunability afforded by formyl substitution.
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