TFA dichloromethane water → HCID 178519239, compound

Participants

Reaction Steps

The route that employs a dipyrromethane-monocarbinol bearing the acetal at the 5-position begins with dipyrromethane 2. Treatment of 2 under the standard conditions for 1-acylation16 with pyridyl thioester 6 afforded the 1-acyldipyrromethane 7 in 72% yield. Reduction of 7 with NaBH4 and self-condensation16,21 of the resulting dipyrromethane-monocarbinol 7-OH in the presence of InCl3 followed by oxidation with DDQ gave porphyrin 8 in 14% yield. Hydrolysis of the two acetal groups in porphyrin 8 with CH2Cl2/TFA/H2O (10:1:1) gave 5,15-diformylporphyrin 9 in 90% yield (Scheme 2).

Provenance & Evidence