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Literature DB >> 21888327

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

Suvi T M Orr¹, Jianhua Tian, Meike Niggemann, Stephen F Martin.

Abstract

The tetracyclic core of the lundurine family of alkaloids has been synthesized by a novel approach that features a double ring-closing olefin metathesis to form the five-and eight-membered rings.

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Year: 2011 PMID： 21888327 PMCID： PMC3184365 DOI： 10.1021/ol201980r

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

21 in total

1. 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

2. 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

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

Authors: Ian C Stewart; Thay Ung; Alexandre A Pletnev; Jacob M Berlin; Robert H Grubbs; Yann Schrodi
Journal: Org Lett Date: 2007-03-23 Impact factor: 6.005

4. 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

5. General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.

Authors: Alexander Deiters; Martin Pettersson; Stephen F Martin
Journal: J Org Chem Date: 2006-08-18 Impact factor: 4.354

6. Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor.

Authors: T E D'Ambra; K G Estep; M R Bell; M A Eissenstat; K A Josef; S J Ward; D A Haycock; E R Baizman; F M Casiano; N C Beglin
Journal: J Med Chem Date: 1992-01 Impact factor: 7.446

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

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

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

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

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

5. General strategy for the syntheses of corynanthe, tacaman, and oxindole alkaloids.

6. Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, (aminoalkyl)indole agonists of the cannabinoid receptor.

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

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

9. A general synthesis of substituted indoles from cyclic enol ethers and enol lactones.

10. Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis.

1. Synthetic studies toward lapidilectine-type Kopsia alkaloids.