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A new access to enantiopure β-hydroxylated piperidines from N-Boc-2-acyloxazolidines. Application to the synthesis of (−)-desoxoprosopinine and (+)-pseudoconhydrine

✍ Scribed by Claude Agami; François Couty; Hubert Lam; Hélène Mathieu

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

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✦ Synopsis

The synthesis of (-)-desoxoprosopinine and (+)-pseudoconhydrine were achieved from a common oxazolidine precursor. The three ste~eocenters present in (-)-desoxoprosopinine as well as the two stereocemers of (+)-pseudoconhydrine were created in highly stereoselective ways. The stereoselectivity observed during the reduction of the ketone moiety in the starting oxazolidine was dependent on the occurrence of a chelated intermediate. The others stereocenters arose from stereoselective reductions or alkylations of intermediate iminium ions.

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