Please use this identifier to cite or link to this item: https://doi.org/10.1002/ejoc.201300227
Title: Bisannulation of 2,3-dichloro-1,4-naphthoquinone with o-nitrophenylacetic acid derivatives: A succinct synthesis of the ABCD ring system of alpkinidine
Authors: Buccini, M.
Jeow, S.Y.
Byrne, L.
Skelton, B.W.
Nguyen, T.M.
Chai, C.L.L. 
Piggott, M.J.
Keywords: Alkaloids
Annulation
Natural products
Nitrogen heterocycles
Synthesis design
Issue Date: Jun-2013
Citation: Buccini, M., Jeow, S.Y., Byrne, L., Skelton, B.W., Nguyen, T.M., Chai, C.L.L., Piggott, M.J. (2013-06). Bisannulation of 2,3-dichloro-1,4-naphthoquinone with o-nitrophenylacetic acid derivatives: A succinct synthesis of the ABCD ring system of alpkinidine. European Journal of Organic Chemistry (16) : 3232-3240. ScholarBank@NUS Repository. https://doi.org/10.1002/ejoc.201300227
Abstract: Three bisannulation strategies have been used to rapidly construct pentacyclic benzo-fused pyrrolo[4,3,2-mn]acridines, similar to several biologically active natural products. The key steps involve Michael substitution of 2,3-dichloro-1,4-naphthoquinone with o-nitrophenylacetic acid derivatives, followed by domino amino-Michael substitutions/cyclisations. The most efficient of these syntheses provided a model compound (1) including the ABCD ring-system of alpkinidine, in just three steps and 55 % overall yield. An annulation strategy involving successive Michael and amino-Michael substitution reactions of 2,3-dichloro-1,4-naphthoquinone has been used to rapidly construct the ABCD ring system of the pyrroloacridine natural product alpkinidine. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: European Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/105705
ISSN: 1434193X
DOI: 10.1002/ejoc.201300227
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