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Literature DB >> 22926836

Total synthesis of (-)-jiadifenin.

Yang Yang¹, Xingnian Fu, Jianwei Chen, Hongbin Zhai.

Abstract

As easy as ABCD: (-)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4'-bromo-2'-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland-Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson-Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.

Entities: Chemical Disease

Mesh：

Substances：
Sesquiterpenes
jiadifenin

Year: 2012 PMID： 22926836 DOI： 10.1002/anie.201203176

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

14 in total

Review 1. Neurotrophic natural products: chemistry and biology.

Authors: Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal: Angew Chem Int Ed Engl Date: 2013-12-18 Impact factor: 15.336

2. A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

Authors: Tian Qin; Josep Cornella; Chao Li; Lara R Malins; Jacob T Edwards; Shuhei Kawamura; Brad D Maxwell; Martin D Eastgate; Phil S Baran
Journal: Science Date: 2016-04-21 Impact factor: 47.728

3. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

Authors: Kevin Hung; Matthew L Condakes; Luiz F T Novaes; Stephen J Harwood; Takahiro Morikawa; Zhi Yang; Thomas J Maimone
Journal: J Am Chem Soc Date: 2019-02-11 Impact factor: 15.419

4. Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors: Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal: Chem Rev Date: 2016-03-28 Impact factor: 60.622

5. Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.

Authors: Xiayun Cheng; Glenn C Micalizio
Journal: J Am Chem Soc Date: 2016-01-25 Impact factor: 15.419

10. Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation.

Authors: Lynnie Trzoss; Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal: Beilstein J Org Chem Date: 2013-06-12 Impact factor: 2.883

Total synthesis of (-)-jiadifenin.

Review 1. Neurotrophic natural products: chemistry and biology.

2. A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents.

3. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

4. Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

5. Synthesis of Neurotrophic Seco-prezizaane Sesquiterpenes (1R,10S)-2-Oxo-3,4-dehydroneomajucin, (2S)-Hydroxy-3,4-dehydroneomajucin, and (-)-Jiadifenin.

6. Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species.

7. Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

8. Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Review 9. Total synthesis of complex terpenoids employing radical cascade processes.

10. Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation.