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.O-1,5(7,11))hexadec-7(11)ene-2,6-dione (C15H18O4)

Authors
Ranganathan, S Muraleedharan, KM Rao, CC Vairamani, M Karle, IL
Citation
S. Ranganathan et al., 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.O-1,5(7,11))hexadec-7(11)ene-2,6-dione (C15H18O4), ORG LETT, 3(16), 2001, pp. 2447-2449
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
16
Year of publication
2001
Pages
2447 - 2449
Database
ISI
SICI code
1523-7060(20010809)3:16<2447:OTOT(C>2.0.ZU;2-#
Abstract
[GRAPHICS] Ozonolysis of I largely results in 2 and 3, having features similar to seve ral classes of natural products. The retention of the C-15 pericycle sugges ts preference for the cleavage of pi -bonds endo to the cyclopentane ring. This unique property of trindane offers opportunities for synthesis of comp lex natural products from this hydrocarbon that can be made in quantity by acid-catalyzed trimerizatiion of cyclopentanone.