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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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