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Synthesis of azaspiro[4.5]decane systems by oxidative cyclization of olefinic precursors

✍ Scribed by María J. Martín-López; Francisco Bermejo

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
651 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The synthesis of 6-benzyloxycarbonyl-l-oxa-6-azaspiro[4.5]decan-2-one ( 17) and 6benzyloxycarbonyl-l,6-diazaspiro[4.5]decan-2-one (18) from the D,L-pipecolic acid derivative 10, is described. The synthesis of (+)-6-benzyl-3-methyl-l,6-diazaspiro[4.5]dec-3-ene-2,7-dione (29), the spiro structural unit of (+)-pandamarine (8) has been achieved by oxidative cylization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamidobutylidene)-3-methyl-3-pyrrolin-2-one ( 25)and ( 26). The stereoselectivity obtained in the intramolecular cyclization process has also been discussed.

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