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Literature DB >> 19397301

Synthesis of macrocyclic beta-strand templates by ring closing metathesis.

Andrew D Abell¹, Nathan A Alexander, Steven G Aitken, Hongyuan Chen, James M Coxon, Matthew A Jones, Stephen B McNabb, Andrew Muscroft-Taylor.

Abstract

We report the synthesis of macrocycles 1-6 via ring closing metathesis of dienes 7-12. Addition of chlorodicyclohexylborane to thermal and microwave assisted RCM of dienes 8 and 9 markedly improves the yield. The geometric isomers of macrocycles 1-3 and 5 have been assigned using X-ray crystallography and NMR.

Entities: Chemical

Year: 2009 PMID： 19397301 DOI： 10.1021/jo802723w

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

6 in total

1. Optimized Ring Closing Metathesis Reaction Conditions To Suppress Desallyl Side Products in the Solid-Phase Synthesis of Cyclic Peptides Involving Tyrosine(O-allyl).

Authors: Solomon A Gisemba; Jane V Aldrich
Journal: J Org Chem Date: 2020-01-13 Impact factor: 4.354

2. Total Synthesis and Structural Reassignment of Laingolide A.

Authors: Fusong Wu; Tao Zhang; Jie Yu; Yian Guo; Tao Ye
Journal: Mar Drugs Date: 2021-04-27 Impact factor: 5.118

3. Unraveling the interplay of backbone rigidity and electron rich side-chains on electron transfer in peptides: the realization of tunable molecular wires.

Authors: John R Horsley; Jingxian Yu; Katherine E Moore; Joe G Shapter; Andrew D Abell
Journal: J Am Chem Soc Date: 2014-08-20 Impact factor: 15.419

Synthesis of macrocyclic beta-strand templates by ring closing metathesis.

1. Optimized Ring Closing Metathesis Reaction Conditions To Suppress Desallyl Side Products in the Solid-Phase Synthesis of Cyclic Peptides Involving Tyrosine(O-allyl).

2. Total Synthesis and Structural Reassignment of Laingolide A.

3. Unraveling the interplay of backbone rigidity and electron rich side-chains on electron transfer in peptides: the realization of tunable molecular wires.

Review 4. Structural and pharmacological effects of ring-closing metathesis in peptides.

Review 5. Macrocyclic drugs and synthetic methodologies toward macrocycles.

6. Stereoselective synthesis of macrocyclic peptides via a dual olefin metathesis and ethenolysis approach.