Spiroaxillarone A, a Symmetric Spirobisnaphthalene with an Original Skeleton from Cyanotis axillaris

The first representative of a new type of spirobisnaphthalene with a previously unknown skeletal system, Spiroaxillarone A (1), was isolated from Cyanotis axillaris. The planar structure was determined through analysis of spectroscopic evidence, while electronic circular dichroism (ECD) calculations...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (20), p.8344-8348
Main Authors: Wisetsai, Awat, Lekphrom, Ratsami, Boonmak, Jaursup, Youngme, Sujittra, Schevenels, Florian T
Format: Article
Language:English
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Summary:The first representative of a new type of spirobisnaphthalene with a previously unknown skeletal system, Spiroaxillarone A (1), was isolated from Cyanotis axillaris. The planar structure was determined through analysis of spectroscopic evidence, while electronic circular dichroism (ECD) calculations were used to determine its absolute configuration. The structure of 1 was further confirmed through X-ray diffraction studies of its tetrabromobenzoate derivative (1a). Spiroaxillarone A exhibited significant antimalarial activity against resistant Plasmodium falciparum (IC50 = 2.32 μM).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03122