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Cavicularin

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Cavicularin
Names
IUPAC name 9,10,18,19-Tetrahydro-5,8:15,17-diethenobenzonaphthoxacyclotetradecin-3,12,21-triol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-26-15-23-19(14-25(26)31)6-5-17-7-12-24(30)28(22)27(17)23/h2-3,7-15,29-31H,1,4-6H2Key: URQGPPCZQAUJRX-UHFFFAOYSA-N
  • InChI=1/C28H22O4/c29-20-8-11-22-18(13-20)4-1-16-2-9-21(10-3-16)32-26-15-23-19(14-25(26)31)6-5-17-7-12-24(30)28(22)27(17)23/h2-3,7-15,29-31H,1,4-6H2Key: URQGPPCZQAUJRX-UHFFFAOYAK
SMILES
  • c1cc2ccc1CCc3cc(ccc3-c4c(ccc5c4-c6cc(c(cc6CC5)O)O2)O)O
Properties
Chemical formula C28H22O4
Molar mass 422.480 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
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 due to the presence of planar chirality and axial chirality. The specific rotation for (+)-cavicularin is +168.2°. 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.

File:Cavicularin.gif
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.

File:Riccardin.gif
Riccardin C, flat molecule representation

References

  1. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. 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:10.1002/anie.200500466. PMID 15900530.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Kostiuk, S. L., Woodcock, T., Dudin, L. F., Howes, P. D. and Harrowven, D. C. (2011), Unified Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration. Chemistry - A European Journal, 17: 10906–10915. doi:10.1002/chem.201101550
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