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)).
[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.
Ranganathan
S
S
Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
Muraleedharan
K M
KM
Rao
C C
CC
Vairamani
M
M
Karle
I L
IL
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000737:chemistry*
C434305:12-hydroxy-16-oxatetracyclo(10.3.1.0.(1,5)0(7,11))hexadec-7(11)ene-2,6-dione; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D011083:Polycyclic Compounds; C434306:bicyclo(10.3.0)pentadec-1(12)ene-2,6,7,11-tetrone