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1985•Canadian Journal of ChemistryOpen access

Lactams of sparteine

W. Marek Golebiewskl, Ian D. Spenser

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Abstract

(2,2-2H2)Sparteine, (6-2H)sparteine, (10,10-2H2)sparteine, (15,15-2H2)sparteine, (17α-2H)sparteine, (17β-2H)sparteine, (17,17-2H2)sparteine, (17α-2H)lupanine, and (17β-2H)lupanine were prepared and employed to assign the 1H nmr spectrum of sparteine. Contrary to a published report, photochemical oxidation of sparteine does not lead to 15-oxosparteine but to 17-oxosparteine.

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(2,2-2H2)Sparteine, (6-2H)sparteine, (10,10-2H2)sparteine, (15,15-2H2)sparteine, (17α-2H)sparteine, (17β-2H)sparteine, (17,17-2H2)sparteine, (17α-2H)lupanine, and (17β-2H)lupanine were prepared and employed to assign the 1H nmr spectrum of sparteine. Contrary to a published report, photochemical oxidation of sparteine does not lead to 15-oxosparteine but to 17-oxosparteine.

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Available abstract

(2,2-2H2)Sparteine, (6-2H)sparteine, (10,10-2H2)sparteine, (15,15-2H2)sparteine, (17α-2H)sparteine, (17β-2H)sparteine, (17,17-2H2)sparteine, (17α-2H)lupanine, and (17β-2H)lupanine were prepared and employed to assign the 1H nmr spectrum of sparteine. Contrary to a published report, photochemical oxidation of sparteine does not lead to 15-oxosparteine but to 17-oxosparteine.

Key concepts: Sparteine, Chemistry, Stereochemistry

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