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Virosaines A and B, two new birdcage-shaped Securinega alkaloids with an unprecedented skeleton from Flueggea virosa.

Research paper by Bing-Xin BX Zhao, Ying Y Wang, Dong-Mei DM Zhang, Xiao-Jun XJ Huang, Liang-Liang LL Bai, Yan Y Yan, Jia-Mei JM Chen, Tong-Bu TB Lu, Yi-Tao YT Wang, Qing-Wen QW Zhang, Wen-Cai WC Ye

Indexed on: 02 Jun '12Published on: 02 Jun '12Published in: Organic Letters



Abstract

Two new Securinega alkaloids, virosaines A (1) and B (2), were isolated from the twigs and leaves of Flueggea virosa. The structures and absolute configurations were elucidated by means of NMR, X-ray diffraction, and CD analyses. Compounds 1 and 2 represent the first examples of Securinega alkaloids bearing a 7-oxa-1-azabicyclo[3.2.1]octane ring system, whose plausible biogenetic pathways were also proposed.