Literature DB >> 22711939

Facile Syntheses of Substituted, Conformationally-Constrained Benzoxazocines and Benzazocines via Sequential Multicomponent Assembly and Cyclization.

James J Sahn1, Stephen F Martin.   

Abstract

A multicomponent assembly process (MCAP) was utilized to prepare versatile intermediates that are suitably functionalized for subsequent cyclizations via Ullmann and Heck reactions to efficiently construct substituted 2,6-methanobenzo[b][1,5]oxazocines and 1,6-methanobenzo[c]azocines, respectively. The intramolecular Ullmann cyclization was conducted in tandem with an intermolecular arylation that enabled the rapid syntheses of a number of O-functionalized methanobenzoxazocines.

Entities:  

Year:  2011        PMID： 22711939      PMCID： PMC3375694          DOI： 10.1016/j.tetlet.2011.10.022

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  22 in total

1.  Facile and unified approach to skeletally diverse, privileged scaffolds.

Authors:  James J Sahn; Justin Y Su; Stephen F Martin
Journal:  Org Lett       Date:  2011-04-22       Impact factor: 6.005

2.  Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

Authors:  David G Washburn; Richard W Heidebrecht; Stephen F Martin
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

3.  Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Authors:  Rodrigo B Andrade; Stephen F Martin
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

4.  Synthesis of Diverse Heterocyclic Scaffolds via Tandem Additions to Imine Derivatives and Ring-Forming Reactions.

Authors:  James D Sunderhaus; Chris Dockendorff; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

5.  Synthesis and pharmacological properties of 1,2,3,4,5,6-hexahydro-1,6-methano-2-benzazocines.

Authors:  P H Mazzocchi; B C Stahly
Journal:  J Med Chem       Date:  1981-04       Impact factor: 7.446

6.  Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis.

Authors:  Jason A Deck; Stephen F Martin
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

7.  Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds.

Authors:  James D Sunderhaus; Stephen F Martin
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

8.  Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

Authors:  Christopher E Neipp; Stephen F Martin
Journal:  J Org Chem       Date:  2003-11-14       Impact factor: 4.354

9.  Toward the total synthesis of FR901483: concise synthesis of the azatricyclic skeleton.

Authors:  Suvi T M Simila; Stephen F Martin
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

10.  An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.

Authors:  Ryan A Altman; Alexandr Shafir; Alice Choi; Phillip A Lichtor; Stephen L Buchwald
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354
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  9 in total

1.  Application of a sequential multicomponent assembly process/huisgen cycloaddition strategy to the preparation of libraries of 1,2,3-triazole-fused 1,4-benzodiazepines.

Authors:  James R Donald; Rebekah R Wood; Stephen F Martin
Journal:  ACS Comb Sci       Date:  2012-02-01       Impact factor: 3.784

2.  Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.

Authors:  Simon Hardy; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-10-07       Impact factor: 2.457

Review 3.  Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification.

Authors:  James J Sahn; Brett A Granger; Stephen F Martin
Journal:  Org Biomol Chem       Date:  2014-08-19       Impact factor: 3.876

4.  Sigma 2 Receptor/Tmem97 Agonists Produce Long Lasting Antineuropathic Pain Effects in Mice.

Authors:  James J Sahn; Galo L Mejia; Pradipta R Ray; Stephen F Martin; Theodore J Price
Journal:  ACS Chem Neurosci       Date:  2017-07-13       Impact factor: 4.418

5.  Applications of Ring Closing Metathesis. Total Synthesis of (±)-Pseudotabersonine.

Authors:  Bo Cheng; James D Sunderhaus; Stephen F Martin
Journal:  Tetrahedron       Date:  2015-09-30       Impact factor: 2.457

6.  Multicomponent assembly processes for the synthesis of diverse yohimbine and corynanthe alkaloid analogues.

Authors:  Brett A Granger; Zhiqian Wang; Kyosuke Kaneda; Zhenglai Fang; Stephen F Martin
Journal:  ACS Comb Sci       Date:  2013-06-04       Impact factor: 3.784

7.  RECENT SYNTHETIC DEVELOPMENTS AND APPLICATIONS OF THE ULLMANN REACTION. A REVIEW.

Authors:  Hao Lin; Dianqing Sun
Journal:  Org Prep Proced Int       Date:  2013       Impact factor: 1.628

8.  Expedient synthesis of norbenzomorphan library via multicomponent assembly process coupled with ring-closing reactions.

Authors:  James J Sahn; Stephen F Martin
Journal:  ACS Comb Sci       Date:  2012-08-20       Impact factor: 3.784

9.  Design, Synthesis, and Evaluation of Novel Anti-Trypanosomal Compounds.

Authors:  Lance T Lepovitz; Alan R Meis; Sarah M Thomas; Justin Wiedeman; Alexandra Pham; Kojo Mensa-Wilmot; Stephen F Martin
Journal:  Tetrahedron       Date:  2020-03-03       Impact factor: 2.457
  9 in total

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