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Molecules 2008, 13(12), 2935-2947; doi:10.3390/molecules13122935
Article

Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one

1,* , 1, 1, 1 and 2
1 Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand 2 Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand
* Author to whom correspondence should be addressed.
Received: 8 November 2008 / Revised: 19 November 2008 / Accepted: 25 November 2008 / Published: 28 November 2008
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
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Abstract

The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.
Keywords: Alkaloid; Amidic aporphine; Isoquinoline; Synthesis; Antimicrobial activity Alkaloid; Amidic aporphine; Isoquinoline; Synthesis; Antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Nimgirawath, S.; Udomputtimekakul, P.; Pongphuttichai, S.; Wanbanjob, A.; Taechowisan, T. Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one. Molecules 2008, 13, 2935-2947.

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