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Title: Four Routes to 3-(3-Methoxy-1,3-dioxopropyl)pyrrole, a Core Motif of Rings C and E in Photosynthetic Tetrapyrroles
The photosynthetic tetrapyrroles share a common structural feature comprised of a β-ketoester motif embedded in an exocyclic ring (ring E). As part of a total synthesis program aimed at preparing native structures and analogues, 3-(3-methoxy-1,3-dioxopropyl)pyrrole was sought. The pyrrole is a precursor to analogues of ring C and the external framework of ring E. Four routes were developed. Routes 1–3 entail a Pd-mediated coupling process of a 3-iodopyrrole with potassium methyl malonate, whereas route 4 relies on electrophilic substitution of TIPS-pyrrole with methyl malonyl chloride. Together, the four routes afford considerable latitude. A long-term objective is to gain the capacity to create chlorophylls and bacteriochlorophylls and analogues thereof by facile de novo means for diverse studies across the photosynthetic sciences.  more » « less
Award ID(s):
2054497
PAR ID:
10520395
Author(s) / Creator(s):
; ; ; ; ; ;
Publisher / Repository:
Molecules
Date Published:
Journal Name:
Molecules
Volume:
28
Issue:
3
ISSN:
1420-3049
Page Range / eLocation ID:
1323
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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