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Literature DB >> 12967315

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

David G Washburn¹, Richard W Heidebrecht, Stephen F Martin.

Abstract

[reaction: see text] A synthesis of the 6-aza[3.2.1]bicyclooctene (-)-2 has been completed by a short sequence of reactions that required only six operations from (S)-malic acid and featured a novel ring-closing metathesis to form the bridged bicyclic ring. Because 2 was previously converted into (-)-peduncularine (1), its preparation constitutes a formal enantioselective synthesis of 1.

Entities: Chemical

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Year: 2003 PMID： 12967315 DOI： 10.1021/ol0354066

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

13 in total

1. 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

2. Concise, enantioselective total synthesis of (-)-alstonerine.

Authors: Kenneth A Miller; Stephen F Martin
Journal: Org Lett Date: 2007-02-14 Impact factor: 6.005

3. Novel approach to the lundurine alkaloids: synthesis of the tetracyclic core.

Authors: Suvi T M Orr; Jianhua Tian; Meike Niggemann; Stephen F Martin
Journal: Org Lett Date: 2011-09-02 Impact factor: 6.005

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

Authors: Stephen F Martin
Journal: J Org Chem Date: 2017-09-15 Impact factor: 4.354

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

Authors: James J Sahn; Stephen F Martin
Journal: Tetrahedron Lett Date: 2011-12-21 Impact factor: 2.415

10. The Pauson-Khand Reaction as a New Entry to the Synthesis of Bridged Bicyclic Heterocycles: Application to the Enantioselective Total Synthesis of (-)-Alstonerine.

Authors: Kenneth A Miller; Charles S Shanahan; Stephen F Martin
Journal: Tetrahedron Date: 2008 Impact factor: 2.457

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

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

2. Concise, enantioselective total synthesis of (-)-alstonerine.

3. Novel approach to the lundurine alkaloids: synthesis of the tetracyclic core.

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

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

6. Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.

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

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

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

10. The Pauson-Khand Reaction as a New Entry to the Synthesis of Bridged Bicyclic Heterocycles: Application to the Enantioselective Total Synthesis of (-)-Alstonerine.