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Synthesis of 5-,6-, and 7-deutero sparteines

✍ Scribed by Claus O. Meese; Thomas Ebner

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
263 KB
Volume
25
Category
Article
ISSN
0022-2135

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✦ Synopsis

Kinetically controlled 'H/'H exchange at carbon atom 5 of (-)-1.6-dehydrosparteinium monoperchlorate ua) followed by sodium borohydride or sodium borodeuteride reduction of the iminium double bond gave optically active 5,5-('H,)-sparteine 0 and 5.5,6-('Hs)sparteine (16). respectively. Under thermodynamic control a third deuterium atom was incorporated into 2 at carbon atom 7. Borohydride reduction or rapid re-exchange followed by reduction lead to the novel sparteine analogues 5,5.7-(2Hs)-sparteine UB) and 7-(2H)-sparteine 0. The title compounds have been prepared in 76 to 83 % yield and 89 to 97 % isotopic purity.

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