Asymmetric syntheses of N-acetyl-(R)-coniine and N-Boc-(2R,6R)-solenopsin A via ring-closing metathesis

Ramaiah Kumareswaran, Alfred Hassner

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Asymmetric syntheses of piperidine alkaloids N-acetyl-(R)-coniine and (2R,6R)-trans-solenopsin were achieved utilizing stereoselective additions of allylphenylsulfone to chiral alkyl-N-sulfinylimines and ring-closing olefin metathesis.

Original languageEnglish
Pages (from-to)2269-2276
Number of pages8
JournalTetrahedron Asymmetry
Volume12
Issue number16
DOIs
StatePublished - 13 Sep 2001

Bibliographical note

Funding Information:
Support of this research by a grant from the US–Israel Binational Science Foundation and from the Marcus Center for Medicinal and Pharmaceutical Chemistry is gratefully acknowledged. We thank Professor A. I. Meyers for providing (S)-coniine·HCl as well as HPLC analysis of 12 and 13 , and Dr. H. E. Gottlieb for valuable help with NMR spectra.

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