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Literature DB >> 26300565

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

Bo Cheng¹, James D Sunderhaus¹, Stephen F Martin¹.

Abstract

A novel approach to the Aspidosperma family of alkaloids was developed and applied to a concise total synthesis of (±)-pseudotabersonine that was accomplished in 11 steps. Key transformations include a stepwise variant of a Mannich-like multicomponent assembly process, a double ring-closing metathesis sequence, and a one-pot deprotection/cyclization reaction.

Entities: Chemical Disease Species

Keywords: Alkaloid; Double ring-closing metathesis; Multicomponent assembly process; Total synthesis

Year: 2015 PMID： 26300565 PMCID： PMC4542060 DOI： 10.1016/j.tet.2015.04.082

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

30 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. 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

2. Bran-New Four-Molecule and Five-Molecule Cascade Reactions for One-Pot Synthesis of Pyrano[3,2-c]chromen-5-ones and Spiro[benzo[b][1,4]diazepine-2,2'-pyrano[3,2-c]chromen]-5'-ones under Catalyst- and Solvent-Free Conditions.

Authors: Guoxun Zhu; Zhou Yi; Jie Zhou; Zhiyong Chen; Pengran Guo; Yanying Huang; Jianghan Chen; Huacan Song; Wei Yi
Journal: ACS Omega Date: 2018-10-18

2 in total

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

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

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

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

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

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

6. Total synthesis of indole and dihydroindole alkaloids. I. Introduction and the transannular cyclization appraoch.

7. Highly efficient ruthenium catalysts for the formation of tetrasubstituted olefins via ring-closing metathesis.

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

9. Diversity Oriented Synthesis: Concise Entry to Novel Derivatives of Yohimbine and Corynanthe Alkaloids.

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

1. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

2. Bran-New Four-Molecule and Five-Molecule Cascade Reactions for One-Pot Synthesis of Pyrano[3,2-c]chromen-5-ones and Spiro[benzo[b][1,4]diazepine-2,2'-pyrano[3,2-c]chromen]-5'-ones under Catalyst- and Solvent-Free Conditions.