Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway

Yiwen Zhang; Martin G. Banwell; Paul D. Carr; Anthony C. Willis

doi:10.1021/acs.orglett.5b03672

Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway

Yiwen Zhang, Martin G. Banwell^*, Paul D. Carr, Anthony C. Willis

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

(Chemical Equation Presented). The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).

Original language	English
Pages (from-to)	704-707
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.5b03672
Publication status	Published - 19 Feb 2016

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title = "Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway",

abstract = "(Chemical Equation Presented). The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).",

author = "Yiwen Zhang and Banwell, {Martin G.} and Carr, {Paul D.} and Willis, {Anthony C.}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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doi = "10.1021/acs.orglett.5b03672",

language = "English",

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T1 - Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway

AU - Zhang, Yiwen

AU - Banwell, Martin G.

AU - Carr, Paul D.

AU - Willis, Anthony C.

PY - 2016/2/19

Y1 - 2016/2/19

N2 - (Chemical Equation Presented). The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).

AB - (Chemical Equation Presented). The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).

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U2 - 10.1021/acs.orglett.5b03672

DO - 10.1021/acs.orglett.5b03672

M3 - Article

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VL - 18

SP - 704

EP - 707

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway

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