Efficient syntheses of oncinotine and neooncinotine

Duen Ren Hou, Hsiu Yi Cheng, Eng Chi Wang

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

We have synthesized two natural alkaloids, oncinotine (1) and neooncinotine (2), by means of efficient ring-closing metathesis (RCM) reactions. The required dienes for RCM were assembled from three basic components: 2-allylpiperidine (5), 9-decenoic acid (6), and diamines 7. We developed two different methods to achieve the linkage: the Michael addition of acrylamide and two amidations of succinic anhydride. The Grubbs catalyst was used to form the 17- and 18-membered lactams in 50% and 68% yields, respectively.

Original languageEnglish
Pages (from-to)6094-6099
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number18
DOIs
StatePublished - 3 Sep 2004

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