Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Cavicularin is a natural phenolic secondary metabolite isolated from the liverwort Cavicularia densa. This macrocycle is unusual because it was the first compound isolated from nature displaying optical activity solely due to the presence of planar chirality and axial chirality. The specific rotation for (+)-cavicularin is +168.2°.[1] It is also a very strained molecule. The para-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat boat-like geometry. This type of angle strain in aromatic compounds is normally reserved for synthetic cyclophanes.
Cavicularin, three-dimensional representation
The liverwort was obtained from Mount Ishizuchi in the district of Shikoku. The material was dried for one day, ground to a powder and 5 grams were refluxed in methanol for 4 months [reference needed] to yield 2.5 mg (0.049%) of cavicularin after column chromatography and preparative TLC.
^M. Toyota; T. Yoshida; Y. Kan; S. Takaoka; Y. Asakawa (1996). "(+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph". Tetrahedron Letters. 37 (27): 4745–4748. doi:10.1016/0040-4039(96)00956-2.[dead link]
Cavicularin is a natural phenolic secondary metabolite isolated from the liverwort Cavicularia densa. This macrocycle is unusual because it was the first...
p. 163, ISBN 978-0-321-80322-1 M. Toyota; et al. (1 July 1996). "(+)-Cavicularin: A novel optically active cyclic bibenzyl-dihydrophenanthrene derivative...
monosubstituted paracyclophanes. Nature rarely provides planar chiral molecules, cavicularin being an exception. To assign the configuration of a planar chiral molecule...
This enzyme participates in naphthalene and anthracene degradation. (+)-Cavicularin, a cyclic bibenzyl-dihydrophenanthrene derivative Evans, David A.; Cain...
was prepared by total synthesis together with the strained compound cavicularin. Fugmann, Burkhard; Lang-Fugmann, Susanne; Steglich, Wolfgang (14 May...
natural phenols are chiral. An example of such molecules is catechin. Cavicularin is an unusual macrocycle because it was the first compound isolated from...
few cyclophanes exist in nature. One example of a metacyclophane is cavicularin. Haouamine A is a paracyclophane found in a certain species of tunicate...
await further investigation. The chemical compound cavicularin was isolated from this species. Cavicularin is notable for being the first compound isolated...
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