Organic Letters
Organic Letters
4 years ago

Xylopiana A, a Dimeric Guaiane with a Case-Shaped Core from Xylopia vielana: Structural Elucidation and Biomimetic Conversion

Xylopiana A, a Dimeric Guaiane with a Case-Shaped Core from Xylopia vielana: Structural Elucidation and Biomimetic Conversion
Xu-Wei Zhou, Ming-Hua Yang, Xiao-Bing Wang, Jun Luo, Yong Yin, Jian-Guang Luo, Ling-Yi Kong, Ya-Long Zhang, Lin Wu
Xylopiana A (1), a dimeric guaiane with an unprecedented pentacyclo[5.2.1.01,2.04,5′.05,4′]decane-3,2′-dione core, and three biosynthetically related intermediates, compounds 2–4, were isolated from the leaves of Xylopia vielana. Their structures and absolute configurations were determined by a combination of spectroscopic data, X-ray crystallography, electronic circular dichroism calculations, and chemical conversion. The structure of known vielanin A was revised to be compound 3. Compound 4 exerted a 3.7-fold potentiation effect on doxorubicin susceptibility at the tested concentration of 10 μM.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01276

DOI: 10.1021/acs.orglett.7b01276

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