Organic Letters
Organic Letters
5 years ago

Determination of Taichunamide H and Structural Revision of Taichunamide A

Determination of Taichunamide H and Structural Revision of Taichunamide A
Dehai Li, Feng Li, Tianjiao Zhu, Qianqun Gu, Qian Che, Guojian Zhang, Zhenzhen Zhang
A new indole alkaloid, named taichunamide H (1), was obtained from cultures of the fungus Aspergillus versicolor. With observation of a carbon resonance with a chemical shift of 190.4 ppm, generally thought to be a carbonyl, the structure of 1 was initially proposed to be a diastereomer of taichunamide A that contains a unique spiro-azetidine moiety. Further analysis of compound 1 using X-ray diffraction showed that the spiro-azetidine moiety should be revised as a fused-imine-containing pyrrole ring, with the resonance at 190.4 ppm assigned as an imine carbon. Accordingly, the structure of taichunamide A was also revised.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.8b00061

DOI: 10.1021/acs.orglett.8b00061

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