Literature DB >> 20039614

Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C.

Stephen Philip Fearnley1, Charnsak Thongsornkleeb.   

Abstract

Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, followed by excision of the carbamate, yields (+/-)-2-epi-pumiliotoxin C.

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Year:  2010        PMID： 20039614      PMCID： PMC2872181          DOI： 10.1021/jo902172r

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


  11 in total

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Review 2.  Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds.

Authors:  John W Daly; Thomas F Spande; H Martin Garraffo
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4.  Expedited approach to the vitamin D trans-hydrindane building block from the Hajos dione. Comparative study on various methods for the selective deoxygenation of one of the hydroxy groups in a diol.

Authors:  Paweł Chochrek; Jerzy Wicha
Journal:  J Org Chem       Date:  2007-06-19       Impact factor: 4.354

5.  Intramolecular Diels-Alder reactions of N-substituted oxazolones.

Authors:  Stephen Philip Fearnley; Eleonora Market
Journal:  Chem Commun (Camb)       Date:  2002-03-07       Impact factor: 6.222

6.  Chromium(0)-promoted multicomponent cycloaddition of tethered diynes with cyclic trienes: application to the total synthesis of 9-epi-pentalenic acid.

Authors:  James H Rigby; Mundruppady S Laxmisha; Andrew R Hudson; Charles H Heap; Mary Jane Heeg
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

7.  Total synthesis of (-)-spinosyn A: examination of structural features that govern the stereoselectivity of the key transannular Diels-Alder reaction.

Authors:  SusAnn M Winbush; Dustin J Mergott; William R Roush
Journal:  J Org Chem       Date:  2008-01-24       Impact factor: 4.354

8.  Pumiliotoxin-C and synthetic analogues. A new class of nicotinic antagonists.

Authors:  J E Warnick; P J Jessup; L E Overman; M E Eldefrawi; Y Nimit; J W Daly; E X Albuquerque
Journal:  Mol Pharmacol       Date:  1982-11       Impact factor: 4.436

9.  Decahydroquinoline alkaloids: noncompetitive blockers for nicotinic acetylcholine receptor-channels in pheochromocytoma cells and Torpedo electroplax.

Authors:  J W Daly; Y Nishizawa; W L Padgett; T Tokuyama; P J McCloskey; L Waykole; A G Schultz; R S Aronstam
Journal:  Neurochem Res       Date:  1991-11       Impact factor: 3.996

10.  Occurrence and significance of decahydroquinolines from dendrobatid poison frogs and a myrmicine ant: use of 1H and 13C NMR in their conformational analysis

Authors: 
Journal:  J Nat Prod       Date:  1999-01       Impact factor: 4.050
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