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Molecules 2009, 14(2), 726-737; doi:10.3390/molecules14020726
Article

Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine

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Received: 12 January 2009; in revised form: 9 February 2009 / Accepted: 12 February 2009 / Published: 12 February 2009
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Abstract: (±)-Gusanlung A, 8-oxyberberrubine and (±)-gusanlung D have been synthesized by radical cyclisation of the corresponding 2-aroyl-1-methylenetetra- hydroisoquinolines. The 1H and 13C spectra of (-)-gusanlung D were found to be different from those of synthetic (±)-gusanlung D. Careful analyses of the 13C spectra of (–)-gusanlung A and natural 8-oxyberberrubine also cast doubt on the correctness of the structures previously assigned to these two compounds. (±)-Gusanlung A and (±)-gusanlung D were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.
Keywords: Alkaloid; Protoberberine; Isoquinoline; Synthesis; Antimicrobial activity Alkaloid; Protoberberine; 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.; Apornpisarn, T.; Wanbanjob, A.; Taechowisan, T. Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine. Molecules 2009, 14, 726-737.

AMA Style

Nimgirawath S, Udomputtimekakul P, Apornpisarn T, Wanbanjob A, Taechowisan T. Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine. Molecules. 2009; 14(2):726-737.

Chicago/Turabian Style

Nimgirawath, Surachai; Udomputtimekakul, Phansuang; Apornpisarn, Thitima; Wanbanjob, Asawin; Taechowisan, Thongchai. 2009. "Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine." Molecules 14, no. 2: 726-737.


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