Stereochemistry of 4,5-dihydroxy-alpha-santonin and structure of a new santonin oxidation-product

Paknikar, S.K.; Malik, B.L.; Bates, R.B.; Caldera, S.; Wijayaratne, T.V.

Stereochemistry of 4,5-dihydroxy-alpha-santonin and structure of a new santonin oxidation-product

Paknikar, S.K.; Malik, B.L.; Bates, R.B.; Caldera, S.; Wijayaratne, T.V.

Source : Tetrahedron Letters. 35(44); 1994; 8117-8118.

URI: http://dx.doi.org/10.1016/0040-4039(94)88258-4
http://irgu.unigoa.ac.in/drs/handle/unigoa/660

Date: 1994

Document Type: Journal article

Abstract:

The diol, mp 220 degrees C, obtained by KMnO4 oxidation of alpha-santonin is shown by an nOe study to be 4 beta,5 beta- rather than 4 alpha,5 alpha-dihydroxy-alpha-santonin. On further oxidation with Pb(OAc)(4), it unexpectedly gives a new ketolactone, mp 268 degrees C, which is also obtained as a KMnO4 oxidation product of alpha-santonin.

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