Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

Benoit Bolte; Christopher S. Bryan; Phillip P. Sharp; Soheil Sayyahi; Charly Rihouey; Amy Kendrick; Ping Lan; Martin G. Banwell; Colin J. Jackson; Nicholas J. Fraser; Anthony C. Willis; Jas S. Ward

doi:10.1021/acs.joc.9b02725

Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

Benoit Bolte, Christopher S. Bryan, Phillip P. Sharp, Soheil Sayyahi, Charly Rihouey, Amy Kendrick, Ping Lan, Martin G. Banwell^*, Colin J. Jackson, Nicholas J. Fraser, Anthony C. Willis, Jas S. Ward

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener 2 proving to be the most active.

Original language	English
Pages (from-to)	650-663
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	85
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.9b02725
Publication status	Published - 17 Jan 2020

Access to Document

10.1021/acs.joc.9b02725

Cite this

Bolte, B., Bryan, C. S., Sharp, P. P., Sayyahi, S., Rihouey, C., Kendrick, A., Lan, P., Banwell, M. G., Jackson, C. J., Fraser, N. J., Willis, A. C., & Ward, J. S. (2020). Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway. Journal of Organic Chemistry, 85(2), 650-663. https://doi.org/10.1021/acs.joc.9b02725

@article{839aa7b300f24a5db8536c8b325217ed,

title = "Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway",

abstract = "Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener 2 proving to be the most active.",

author = "Benoit Bolte and Bryan, {Christopher S.} and Sharp, {Phillip P.} and Soheil Sayyahi and Charly Rihouey and Amy Kendrick and Ping Lan and Banwell, {Martin G.} and Jackson, {Colin J.} and Fraser, {Nicholas J.} and Willis, {Anthony C.} and Ward, {Jas S.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2020",

month = jan,

day = "17",

doi = "10.1021/acs.joc.9b02725",

language = "English",

volume = "85",

pages = "650--663",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

Bolte, B, Bryan, CS, Sharp, PP, Sayyahi, S, Rihouey, C, Kendrick, A, Lan, P, Banwell, MG, Jackson, CJ, Fraser, NJ, Willis, AC & Ward, JS 2020, 'Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway', Journal of Organic Chemistry, vol. 85, no. 2, pp. 650-663. https://doi.org/10.1021/acs.joc.9b02725

Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway. / Bolte, Benoit; Bryan, Christopher S.; Sharp, Phillip P. et al.
In: Journal of Organic Chemistry, Vol. 85, No. 2, 17.01.2020, p. 650-663.

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

TY - JOUR

T1 - Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

AU - Bolte, Benoit

AU - Bryan, Christopher S.

AU - Sharp, Phillip P.

AU - Sayyahi, Soheil

AU - Rihouey, Charly

AU - Kendrick, Amy

AU - Lan, Ping

AU - Banwell, Martin G.

AU - Jackson, Colin J.

AU - Fraser, Nicholas J.

AU - Willis, Anthony C.

AU - Ward, Jas S.

PY - 2020/1/17

Y1 - 2020/1/17

N2 - Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener 2 proving to be the most active.

AB - Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with congener 2 proving to be the most active.

UR - http://www.scopus.com/inward/record.url?scp=85076963849&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b02725

DO - 10.1021/acs.joc.9b02725

M3 - Article

SN - 0022-3263

VL - 85

SP - 650

EP - 663

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Total Syntheses of the 3 H-Pyrrolo[2,3- c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

Abstract

Access to Document

Other files and links

Fingerprint

Cite this