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Literature DB >> 22040033

Total synthesis of hirsutellone B via Ullmann-type direct 13-membered macrocyclization.

Hiromi Uchiro¹, Ryo Kato, Yuuki Arai, Miki Hasegawa, Yu Kobayakawa.

Abstract

Total synthesis of Hirsutellone B has been achieved by a convergent synthetic strategy. This synthesis features direct construction of the highly strained 13-membered macrocycle of Hirsutellone B utilizing the Ullmann-type reaction. To the best of our knowledge, this is the first application of macrocyclization utilizing an intramolecular Ullmann-type reaction between an aliphatic alcohol and aryl halide.

Entities: Chemical

Mesh：

Substances：

Year: 2011 PMID： 22040033 DOI： 10.1021/ol202748e

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

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Cited

13 in total

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Review 2. A brief history of antibiotics and select advances in their synthesis.

Authors: Kyriacos C Nicolaou; Stephan Rigol
Journal: J Antibiot (Tokyo) Date: 2017-07-05 Impact factor: 2.649

3. Chirality-matched catalyst-controlled macrocyclization reactions.

Authors: Jaeyeon Hwang; Brandon Q Mercado; Scott J Miller
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4. Xenoacremones D-H, Bioactive Tyrosine-decahydrofluorene Analogues from the Plant-Derived Fungus Xenoacremonium sinensis.

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Journal: Mar Drugs Date: 2022-05-31 Impact factor: 6.085

9. Photoredox Ni-catalyzed peptide C(sp²)-O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization.

Authors: Hyelee Lee; Nicolas C Boyer; Qiaolin Deng; Hai-Young Kim; Tomi K Sawyer; Nunzio Sciammetta
Journal: Chem Sci Date: 2019-04-12 Impact factor: 9.825

Review 10. Macrocyclic drugs and synthetic methodologies toward macrocycles.

Authors: Xufen Yu; Dianqing Sun
Journal: Molecules Date: 2013-05-24 Impact factor: 4.411

Total synthesis of hirsutellone B via Ullmann-type direct 13-membered macrocyclization.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Review 2. A brief history of antibiotics and select advances in their synthesis.

3. Chirality-matched catalyst-controlled macrocyclization reactions.

4. Xenoacremones D-H, Bioactive Tyrosine-decahydrofluorene Analogues from the Plant-Derived Fungus Xenoacremonium sinensis.

5. Toward a synthesis of hirsutellone B by the concept of double cyclization.

6. Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

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

8. Biosynthesis of para-Cyclophane-Containing Hirsutellone Family of Fungal Natural Products.

9. Photoredox Ni-catalyzed peptide C(sp²)-O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization.

Review 10. Macrocyclic drugs and synthetic methodologies toward macrocycles.