Literature DB >> 16709064

Asymmetric synthesis of (-)-nupharamine and (-)-(5S,8R,9S)-5-(3-furyl)-8-methyloctahydroindolizidine from beta-amino ketones and the intramolecular Mannich reaction.

Franklin A Davis1, Manikandan Santhanaraman.   

Abstract

The asymmetric synthesis of the 2,3,6-trisubstituted piperidine core of the antitumor Nuphar alkaloids was readily achieved by using the intramolecular Mannich reaction and a sulfinimine-derived beta-amino ketone.

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Year:  2006        PMID： 16709064     DOI： 10.1021/jo060371j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

Authors:  Hajime Seki; Gunda I Georg
Journal:  European J Org Chem       Date:  2014-06-01

2.  Toward the Synthesis of Nuphar Sesquiterpene Thioalkaloids: Stereodivergent Rhodium-Catalyzed Synthesis of the Thiolane Subunit.

Authors:  Ping Lu; Aaron T Herrmann; Armen Zakarian
Journal:  J Org Chem       Date:  2015-07-28       Impact factor: 4.354

3.  Asymmetric synthesis of substituted tropinones using the intramolecular mannich cyclization reaction and acyclic N-sulfinyl beta-amino ketone ketals.

Authors:  Franklin A Davis; Naresh Theddu; Paul M Gaspari
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

Review 4.  Applications of aryl-sulfinamides in the synthesis of N-heterocycles.

Authors:  Rose Mary Philip; G S Susan Treesa; Salim Saranya; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-06-08       Impact factor: 4.036

5.  Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.

Authors:  Pavol Jakubec; Dane M Cockfield; Madeleine Helliwell; James Raftery; Darren J Dixon
Journal:  Beilstein J Org Chem       Date:  2012-04-16       Impact factor: 2.883
  5 in total

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