jo9b01650_si_002.cif (451.97 kB)
Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls
dataset
posted on 2019-08-20, 20:30 authored by Pengzhi Wang, Khiem Chau Nguyen, Jonathan S. LindseyAs 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.