Synthesis of the Ring
C Pyrrole of Native Chlorophylls
and Bacteriochlorophylls
Pengzhi Wang
Khiem Chau Nguyen
Jonathan S. Lindsey
10.1021/acs.joc.9b01650.s002
https://acs.figshare.com/articles/dataset/Synthesis_of_the_Ring_C_Pyrrole_of_Native_Chlorophylls_and_Bacteriochlorophylls/9696296
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 <i>N</i>-TIPS-pyrrole or with 4-oxo-2-pentene and TosMIC,
affording multi-gram-quantities of this ostensibly simple pyrrole.
2019-08-20 20:30:13
ring D constituent
4- oxo -2-pentene
ring C
2- iodo -3-methyl
Ring C Pyrrole