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. 2005 Dec 8;7(25):5609-12.
doi: 10.1021/ol052269z.

Synthesis of antimicrobial natural products targeting FtsZ: (+/-)-dichamanetin and (+/-)-2' ''-hydroxy-5' '-benzylisouvarinol-B

Sameer Urgaonkar  1 , Henry S La Pierre, Israel Meir, Henrik Lund, Debabrata RayChaudhuri, Jared T Shaw
Affiliations

Synthesis of antimicrobial natural products targeting FtsZ: (+/-)-dichamanetin and (+/-)-2' ''-hydroxy-5' '-benzylisouvarinol-B

Sameer Urgaonkar et al. Org Lett. .

Abstract

[chemical structure: see text]. Two natural products have been synthesized using a ZnCl2-mediated benzylic coupling reaction. Both are potent inhibitors of the GTPase activity of FtsZ, a highly conserved protein that is essential for bacterial cytokinesis.

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Figures

Figure 1
Figure 1
Bacterial cell division and the role of FtsZ
Figure 2
Figure 2
Structures of synthetic (1) and naturally occurring (2 and 3) polyphenolic compounds
Scheme 1
Scheme 1
Retrosynthetic analysis of 2 and 3
Scheme 2
Scheme 2
Synthesis of pinocembrin (4)
Scheme 3
Scheme 3
Aminomethylation of 4 and attempted displacement with phenol to produce 2
Scheme 4
Scheme 4
Synthesis of compound 3
See this image and copyright information in PMC

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