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tricyclopentabenzene

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https://www.readbyqxmd.com/read/11483031/one-step-transformation-of-tricyclopentabenzene-trindane-c-15-h-18-to-bicyclo-10-3-0-pentadec-1-12-ene-2-6-7-11-tetrone-c-15-h-18-o-4-and-its-aldol-product-12-hydroxy-16-oxatetracyclo-10-3-1-0-1-5-0-7-11-hexadec-7-11-ene-2-6-dione-c-15-h-18-o-4
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S Ranganathan, K M Muraleedharan, C C Rao, M Vairamani, I L Karle
[reaction: see text] Ozonolysis of 1 largely results in 2 and 3, having features similar to several classes of natural products. The retention of the C(15) pericycle suggests preference for the cleavage of pi-bonds endo to the cyclopentane ring. This unique property of trindane offers opportunities for synthesis of complex natural products from this hydrocarbon that can be made in quantity by acid-catalyzed trimerization of cyclopentanone.
August 9, 2001: Organic Letters
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