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Literature DB >> 26741730

Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.

Nels C Gerstner¹, Christopher S Adams¹, R David Grigg¹, Maik Tretbar¹, Jared W Rigoli¹, Jennifer M Schomaker¹.

Abstract

Oxidative allene amination provides rapid access to densely functionalized amine-containing stereotriads through highly reactive bicyclic methyleneaziridine intermediates. This strategy has been demonstrated as a viable approach for the construction of the densely functionalized aminocyclitol core of jogyamycin, a natural product with potent antiprotozoal activity. Importantly, the flexibility of oxidative allene amination will enable the syntheses of modified aminocyclitol analogues of the jogyamycin core.

Entities: CellLine Chemical Disease

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Year: 2016 PMID： 26741730 PMCID： PMC4845904 DOI： 10.1021/acs.orglett.5b03453

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

23 in total

1. Modular functionalization of allenes to aminated stereotriads.

Authors: Christopher S Adams; Luke A Boralsky; Ilia A Guzei; Jennifer M Schomaker
Journal: J Am Chem Soc Date: 2012-06-20 Impact factor: 15.419

2. Diastereocontrolled construction of pactamycin's complex ureido triol functional array.

Authors: Justin T Malinowski; Stefan J McCarver; Jeffrey S Johnson
Journal: Org Lett Date: 2012-05-22 Impact factor: 6.005

3. Preparation and biological evaluation of synthetic and polymer-encapsulated congeners of the antitumor agent pactamycin: insight into functional group effects and biological activity.

Authors: Robert J Sharpe; Justin T Malinowski; Federico Sorana; J Christopher Luft; Charles J Bowerman; Joseph M DeSimone; Jeffrey S Johnson
Journal: Bioorg Med Chem Date: 2015-02-21 Impact factor: 3.641

Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.

1. Modular functionalization of allenes to aminated stereotriads.

2. Diastereocontrolled construction of pactamycin's complex ureido triol functional array.

3. Preparation and biological evaluation of synthetic and polymer-encapsulated congeners of the antitumor agent pactamycin: insight into functional group effects and biological activity.

4. Tethered aminohydroxylation using acyclic homo-allylic sulfamate esters and sulfonamides as substrates.

5. Enantioselective synthesis of pactamycin, a complex antitumor antibiotic.

6. Mutasynthesis of fluorinated pactamycin analogues and their antimalarial activity.

7. Deciphering pactamycin biosynthesis and engineered production of new pactamycin analogues.

8. Total synthesis of pactamycin and pactamycate: a detailed account.

9. Diastereoselective synthesis of vicinal tertiary diols.

10. Crystal structure of a bioactive pactamycin analog bound to the 30S ribosomal subunit.

1. Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.

2. Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

3. Fluorinated Amine Stereotriads via Allene Amination.

Review 4. Strategies for the Syntheses of Pactamycin and Jogyamycin.

5. Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.