| Cavicularin | |
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| Molecular formula | C28H22O4 |
| Molar mass | 422.47 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
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Cavicularin is a 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 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. It incorporates a benzene ring that is bent 17° out of planarity. This type of angle strain in aromatic compounds is normally reserved for synthetic cyclophanes.
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Cavicularin, flat molecule representation
The liverwort was obtained from Mt. 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 to yield 2.5 mg (0.049%) of cavicularin after column chromatography and preparative TLC. In 2005, the compound was prepared by total synthesis together with the unstrained compound riccardin C.[2]
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Riccardin C, flat molecule representation
References
- ^ 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: 4745–4748. doi:. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-3V99257-14&_user=1065764&_handle=V-WA-A-W-CD-MsSAYVA-UUA-U-AAWAUAUZVD-AAAYCEAVVD-AZVWVYEDB-CD-U&_fmt=summary&_coverDate=07%2F01%2F1996&_rdoc=32&_orig=browse&_srch=%23toc%235290%231996%23999629972%2339771!&_cdi=5290&view=c&_acct=C000051225&_version=1&_urlVersion=0&_userid=1065764&md5=4e93161113dd5af8dad768dd3c3d842a.
- ^ David C. Harrowven, Timothy Woodcock , Peter D. Howes (2005). "Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration". Angewandte Chemie 44 (25): 3899–3901. doi:. http://www3.interscience.wiley.com/cgi-bin/abstract/110498256/ABSTRACT.
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