Carbophilic 3-component cascades: Access to complex bioactive cyclopropyl diindolylmethanes

Nigel M. Groome; Elghareeb E. Elboray; Martyn W. Inman; H. Ali Dondas; Roger M. Phillips; Colin Kilner; Ronald Grigg

doi:10.1002/chem.201202647

Carbophilic 3-component cascades: Access to complex bioactive cyclopropyl diindolylmethanes

Nigel M. Groome, Elghareeb E. Elboray, Martyn W. Inman, H. Ali Dondas, Roger M. Phillips, Colin Kilner, Ronald Grigg

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

21 Citations (Scopus)

Abstract

Naturally occurring indole-3-carbinol and 3,3-diindolylmethane show bioactivity in a number of disparate disease areas, including cancer, prompting substantial synthetic analogue activity. We describe a new approach to highly functionalised derivatives that starts from allene gas and proceeds via the combination of a three-component Pd⁰-catalysed cascade with a one-pot, three-component carbophilic Pt^II cascade linked to a stereoselective acid-catalysed Mannich-Michael reaction that generates complex cyclopropyl diindolylmethanes which show selective activity against prostate cancer cell lines.

Original language	English
Pages (from-to)	2180-2184
Number of pages	5
Journal	Chemistry - A European Journal
Volume	19
Issue number	6
Early online date	20 Dec 2012
DOIs	https://doi.org/10.1002/chem.201202647
Publication status	Published - 4 Feb 2013
Externally published	Yes

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title = "Carbophilic 3-component cascades: Access to complex bioactive cyclopropyl diindolylmethanes",

abstract = "Naturally occurring indole-3-carbinol and 3,3-diindolylmethane show bioactivity in a number of disparate disease areas, including cancer, prompting substantial synthetic analogue activity. We describe a new approach to highly functionalised derivatives that starts from allene gas and proceeds via the combination of a three-component Pd0-catalysed cascade with a one-pot, three-component carbophilic PtII cascade linked to a stereoselective acid-catalysed Mannich-Michael reaction that generates complex cyclopropyl diindolylmethanes which show selective activity against prostate cancer cell lines.",

keywords = "3-azabicyclo[4.1.0]heptene, diindolylmethanes, enynes, palladium, platinum, prostate cancer",

author = "Groome, {Nigel M.} and Elboray, {Elghareeb E.} and Inman, {Martyn W.} and Dondas, {H. Ali} and Phillips, {Roger M.} and Colin Kilner and Ronald Grigg",

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T1 - Carbophilic 3-component cascades

T2 - Access to complex bioactive cyclopropyl diindolylmethanes

AU - Groome, Nigel M.

AU - Elboray, Elghareeb E.

AU - Inman, Martyn W.

AU - Dondas, H. Ali

AU - Phillips, Roger M.

AU - Kilner, Colin

AU - Grigg, Ronald

PY - 2013/2/4

Y1 - 2013/2/4

N2 - Naturally occurring indole-3-carbinol and 3,3-diindolylmethane show bioactivity in a number of disparate disease areas, including cancer, prompting substantial synthetic analogue activity. We describe a new approach to highly functionalised derivatives that starts from allene gas and proceeds via the combination of a three-component Pd0-catalysed cascade with a one-pot, three-component carbophilic PtII cascade linked to a stereoselective acid-catalysed Mannich-Michael reaction that generates complex cyclopropyl diindolylmethanes which show selective activity against prostate cancer cell lines.

AB - Naturally occurring indole-3-carbinol and 3,3-diindolylmethane show bioactivity in a number of disparate disease areas, including cancer, prompting substantial synthetic analogue activity. We describe a new approach to highly functionalised derivatives that starts from allene gas and proceeds via the combination of a three-component Pd0-catalysed cascade with a one-pot, three-component carbophilic PtII cascade linked to a stereoselective acid-catalysed Mannich-Michael reaction that generates complex cyclopropyl diindolylmethanes which show selective activity against prostate cancer cell lines.

KW - 3-azabicyclo[4.1.0]heptene

KW - diindolylmethanes

KW - enynes

KW - palladium

KW - platinum

KW - prostate cancer

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UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3765

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Carbophilic 3-component cascades: Access to complex bioactive cyclopropyl diindolylmethanes

Abstract

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