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

24 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

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10.1021/acs.joc.9b02725

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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 - https://www.scopus.com/pages/publications/85076963849

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

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