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Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls

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journal contribution
posted on 20.08.2019, 20:30 by Pengzhi Wang, Khiem Chau Nguyen, Jonathan S. Lindsey
As part of a program to develop practical syntheses of members of the family of (bacterio)­chlorophylls, two routes to 2-iodo-3-methyl-4-(3-methoxy-1,3-dioxopropyl)­pyrrole, a precursor of the universal ring C, have been developed. The β-ketoester of ring C is expected to give rise to ring E upon Knoevenagel condensation and Nazarov cyclization with a ring D constituent as demonstrated in an analogue synthesis. Two viable routes were developed beginning with N-TIPS-pyrrole or with 4-oxo-2-pentene and TosMIC, affording multi-gram-quantities of this ostensibly simple pyrrole.