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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-(,50 7,11)hexadec-7(11)ene-2,6-dione (C15H18O4)
, , Chandrashekhar Rao Ch., Vairamani M., Karle I.L.
Published in ACS Publications
Volume: 3
Issue: 16
Pages: 2447 - 2449
matrix presented 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 π-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.
About the journal
JournalOrganic Letters
PublisherACS Publications
Open AccessNo