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Literature DB >> 16287318

Regiospecific and stereoselective syntheses of (+/-)-reserpine and (-)-reserpine.

Gilbert Stork¹, Peng Cho Tang, Michael Casey, Burton Goodman, Masahiro Toyota.

Abstract

Full details of three approaches to an entirely regio- and stereoselective synthesis of the well-known target reserpine are described, culminating in a total synthesis which efficiently meets these requirements.

Entities: Chemical

Mesh：

Substances：
Reserpine

Year: 2005 PMID： 16287318 DOI： 10.1021/ja055744x

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

10 in total

1. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors: Stephen F Martin
Journal: J Org Chem Date: 2017-09-15 Impact factor: 4.354

2. Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors: Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2017-08-22 Impact factor: 15.419

3. Enantioselective total synthesis of (+)-reserpine.

Authors: Naomi S Rajapaksa; Meredeth A McGowan; Matthew Rienzo; Eric N Jacobsen
Journal: Org Lett Date: 2013-01-18 Impact factor: 6.005

4. A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.

Authors: Eric R Miller; M Todd Hovey; Karl A Scheidt
Journal: J Am Chem Soc Date: 2020-01-17 Impact factor: 15.419

Review 5. The Chiral Pool in the Pictet-Spengler Reaction for the Synthesis of β-Carbolines.

Authors: Renato Dalpozzo
Journal: Molecules Date: 2016-05-27 Impact factor: 4.411

6. Multidirectional desymmetrization of pluripotent building block en route to diastereoselective synthesis of complex nature-inspired scaffolds.

Authors: Vunnam Srinivasulu; Paul Schilf; Saleh Ibrahim; Monther A Khanfar; Scott McN Sieburth; Hany Omar; Anusha Sebastian; Raed A AlQawasmeh; Matthew John O'Connor; Taleb H Al-Tel
Journal: Nat Commun Date: 2018-11-26 Impact factor: 14.919

Regiospecific and stereoselective syntheses of (+/-)-reserpine and (-)-reserpine.

1. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

2. Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

3. Enantioselective total synthesis of (+)-reserpine.

4. A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.

Review 5. The Chiral Pool in the Pictet-Spengler Reaction for the Synthesis of β-Carbolines.

6. Multidirectional desymmetrization of pluripotent building block en route to diastereoselective synthesis of complex nature-inspired scaffolds.

Review 7. Multicomponent Reactions for the Synthesis of Active Pharmaceutical Ingredients.

8. A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine.

Review 9. A Review on Platensimycin: A Selective FabF Inhibitor.

10. BIMP-Catalyzed 1,3-Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones.