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

doi:10.3390/molecules13122935

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

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

Surachai Nimgirawath ¹^,* , Phansuang Udomputtimekakul ¹, Samathi Pongphuttichai ¹, Asawin Wanbanjob ¹ and Thongchai Taechowisan 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; in revised form: 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

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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.

AMA 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(12):2935-2947.

Chicago/Turabian Style

Nimgirawath, Surachai; Udomputtimekakul, Phansuang; Pongphuttichai, Samathi; Wanbanjob, Asawin; Taechowisan, Thongchai. 2008. "Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one." Molecules 13, no. 12: 2935-2947.

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