Ranganathan, Subramania ; Muraleedharan, K. M. ; Chandrashekhar Rao, CH. ; Vairamani, M. ; Karle, Isabella L. (2001) One-step transformation of tricyclopentabenzene (trindane, C15H18) to bicyclo(10.3.0)pentadec-1(12)ene- 2,6,7,11-tetrone (C15H18O4) and its aldol product, 12-hydroxy-16-oxatetracyclo(10.3.1.0.1,507,11)hexadec-7(11)ene-2,6-dione (C15H18O4) Organic Letters, 3 (16). pp. 2447-2449. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol010086g
Related URL: http://dx.doi.org/10.1021/ol010086g
Abstract
Ozonolysis of 1 largely results in 2 and 3, having features similar to several classes of natural products. The retention of the C15 pericycle suggests preference for the cleavage of ∏-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 trimerizatiion of cyclopentanone.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 48885 |
| Deposited On: | 20 Jul 2011 06:53 |
| Last Modified: | 20 Jul 2011 06:53 |
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