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| Names | |
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| IUPAC name 9,10,18,19-Tetrahydro-5,8:15,17-diethenobenzo[g]naphth[1,8-bc]oxacyclotetradecin-3,12,21-triol | |
| Identifiers | |
3D model (JSmol) | |
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| UNII | |
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| Properties | |
| C28H22O4 | |
| Molar mass | 422.480 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Cavicularin is anatural phenolicsecondary metabolite isolated from theliverwortCavicularia densa. Thismacrocycle is unusual because it was the first compound isolated from nature displayingoptical activity solely due to the presence ofplanar chirality andaxial chirality. Thespecific rotation for (+)-cavicularin is +168.2°.[1] It is also a verystrained molecule. Thepara-substituted phenol ring is bent about 15° out of planarity, adopting a somewhatboat-like geometry. This type ofangle strain in aromatic compounds is normally reserved for syntheticcyclophanes.
Theliverwort was obtained fromMount Ishizuchi in the district ofShikoku. The material was dried for one day, ground to a powder and 5 grams wererefluxed inmethanol for 4 months[reference needed] to yield 2.5 mg (0.049%) of cavicularin aftercolumn chromatography andpreparative TLC.
In 2005[2] and again in 2011,[3] the compound was prepared bytotal synthesis together with the unstrained compoundriccardin C. In 2013, several other syntheses were reported for it[4][5] and a racemic synthesis.[6]
