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Literature DB >> 16671813

Biomimetic approach to perophoramidine and communesin via an intramolecular cyclopropanation reaction.

Jun Yang¹, Hao Song, Xue Xiao, Jue Wang, Yong Qin.

Abstract

[reaction: see text] Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 16671813 DOI： 10.1021/ol0607138

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

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Cited

12 in total

Review 1. Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

Authors: Barry M Trost; Maksim Osipov
Journal: Chemistry Date: 2015-09-10 Impact factor: 5.236

2. Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F.

Authors: Peng Liu; Jae Hong Seo; Steven M Weinreb
Journal: Angew Chem Int Ed Engl Date: 2010-03-08 Impact factor: 15.336

3. Evolution of a strategy for total synthesis of the marine fungal alkaloid (+/-)-communesin F.

Authors: Jae Hong Seo; Peng Liu; Steven M Weinreb
Journal: J Org Chem Date: 2010-04-16 Impact factor: 4.354

4. 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

5. Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

Authors: Seth L Crawley; Raymond L Funk
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

6. Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

Authors: Chung Whan Lee; Seo-Jung Han; Scott C Virgil; Brian M Stoltz
Journal: Tetrahedron Date: 2015-06-03 Impact factor: 2.457

Biomimetic approach to perophoramidine and communesin via an intramolecular cyclopropanation reaction.

Review 1. Recent Advances on the Total Syntheses of Communesin Alkaloids and Perophoramidine.

2. Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F.

3. Evolution of a strategy for total synthesis of the marine fungal alkaloid (+/-)-communesin F.

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

5. Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

6. Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

7. Synthetic studies on perophoramidine and the communesins: construction of the vicinal quaternary stereocenters.

8. Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.

9. Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.

10. A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.