Literature DB >> 19572008

Diastereoselective Synthesis of a Highly Substituted cis-Decahydroquinoline via a Knoevenagel Condensation.

Junfeng Huang1, Stephen C Bergmeier.   

Abstract

A diastereoselective approach to 3,7,8-trisubstituted cis-decahydroquinolines is described. This ring system forms the core of rings B and E of the norditerpenoid alkaloid methyllycaconitine. This approach starts with a known disubsituted cyclohexene. The remaining carbons are attached via a Knoevenagel condensation followed by an intramolecular lactam formation. The stereochemistry of the substituents is controlled by the cis-substitution of the starting cyclohexene ring.

Entities:  

Year:  2008        PMID： 19572008      PMCID： PMC2597876          DOI： 10.1016/j.tet.2008.04.073

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  18 in total

1.  A Tandem Horner-Emmons Olefination-Conjugate Addition Approach to the Synthesis of 1,5-Disubstituted-6-azabicyclo[3.2.1]octanes Based on the AE Ring Structure of the Norditerpenoid Alkaloid Methyllycaconitine.

Authors:  David J. Callis; Noel F. Thomas; David P. J. Pearson; Barry V. L. Potter
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

2.  Structure-activity studies of bicyclic and tricyclic analogues of methyllycaconitine.

Authors:  A R Davies; D J Hardick; I S Blagbrough; B V Potter; A J Wolstenholme; S Wonnacott
Journal:  Biochem Soc Trans       Date:  1997-08       Impact factor: 5.407

3.  Methyllycaconitine and (+)-anatoxin-a differentiate between nicotinic receptors in vertebrate and invertebrate nervous systems.

Authors:  D R Macallan; G G Lunt; S Wonnacott; K L Swanson; H Rapoport; E X Albuquerque
Journal:  FEBS Lett       Date:  1988-01-04       Impact factor: 4.124

4.  [Cholinesterase inhibition by huperzine B].

Authors:  H Xu; X C Tang
Journal:  Zhongguo Yao Li Xue Bao       Date:  1987-01

5.  Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis.

Authors:  T Shioiri; K Ninomiya; S Yamada
Journal:  J Am Chem Soc       Date:  1972-08-23       Impact factor: 15.419

6.  Methyllycaconitine: a selective probe for neuronal alpha-bungarotoxin binding sites.

Authors:  J M Ward; V B Cockcroft; G G Lunt; F S Smillie; S Wonnacott
Journal:  FEBS Lett       Date:  1990-09-17       Impact factor: 4.124

7.  Structure-activity studies with ring E analogues of methyllycaconitine on bovine adrenal alpha3beta4* nicotinic receptors.

Authors:  Darrell L Bryant; R Benjamin Free; Sara M Thomasy; David J Lapinsky; Khadiga A Ismail; Susan B McKay; Stephen C Bergmeier; Dennis B McKay
Journal:  Neurosci Res       Date:  2002-01       Impact factor: 3.304

8.  Analogs of methyllycaconitine as novel noncompetitive inhibitors of nicotinic receptors: pharmacological characterization, computational modeling, and pharmacophore development.

Authors:  Dennis B McKay; Cheng Chang; Tatiana F González-Cestari; Susan B McKay; Raed A El-Hajj; Darrell L Bryant; Michael X Zhu; Peter W Swaan; Kristjan M Arason; Aravinda B Pulipaka; Crina M Orac; Stephen C Bergmeier
Journal:  Mol Pharmacol       Date:  2007-02-16       Impact factor: 4.436

9.  Preliminary synthetic studies of methyllycaconitine, a potent nicotinic acetylcholine receptor antagonist: rapid syntheses of AE-bicyclic analogues.

Authors:  P A Coates; I S Blagbrough; M G Rowan; D P Pearson; T Lewis; B V Potter
Journal:  J Pharm Pharmacol       Date:  1996-02       Impact factor: 3.765

10.  Structure activity studies of ring E analogues of methyllycaconitine. Part 2: Synthesis of antagonists to the alpha3beta4* nicotinic acetylcholine receptors through modifications to the ester.

Authors:  Stephen C Bergmeier; Khadiga A Ismail; Kristjan M Arason; Susan McKay; Darrell L Bryant; Dennis B McKay
Journal:  Bioorg Med Chem Lett       Date:  2004-07-16       Impact factor: 2.823
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