Efficient, asymmetric synthesis of (-)-isooncinotine

Hsiu Yi Cheng, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Asymmetric synthesis of (-)-isooncinotine, a 22-membered lactam of spermidine alkaloid, starting from resolution of 2-piperidineethanol with (S)-10-camphorsulfonic acid is reported. Michael addition, amidations, and aluminum hydride reduction were applied to form the moiety of spermidine. Retro-Michael addition was observed when β-amido- and β-amino-propionitriles were reduced by LAH. The effects of LAH versus AlH3 were discussed. The synthesis of the skeleton of this macrolide is achieved with ring-closing metathesis of the diene prepared from acylation of the spermidine.

Original languageEnglish
Pages (from-to)3000-3005
Number of pages6
JournalTetrahedron
Volume63
Issue number14
DOIs
StatePublished - 2 Apr 2007

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