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Literature DB >> 19839571

Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies.

Abstract

An expeditious synthesis of erythronolide A is documented. Key steps of the approach include two magnesium-mediated nitrile oxide cycloadditions, a chelation-controlled Grignard reaction, and a Sharpless asymmetric dihydroxylation.

Entities: Chemical

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Year: 2009 PMID： 19839571 DOI： 10.1021/jo901817b

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

8 in total

1. Direct entry to erythronolides via a cyclic bis[allene].

Authors: Kai Liu; Hiyun Kim; Partha Ghosh; Novruz G Akhmedov; Lawrence J Williams
Journal: J Am Chem Soc Date: 2011-09-06 Impact factor: 15.419

2. Progress toward a Convergent, Asymmetric Synthesis of Jervine.

Authors: Blane P Zavesky; Pedro De Jesús Cruz; Jeffrey S Johnson
Journal: Org Lett Date: 2020-04-14 Impact factor: 6.005

3. Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors: Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal: J Am Chem Soc Date: 2016-04-26 Impact factor: 15.419

8. Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.

Authors: Michael Schneider; Matthieu J R Richter; Erick M Carreira
Journal: J Am Chem Soc Date: 2020-10-06 Impact factor: 15.419

8 in total

Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies.

1. Direct entry to erythronolides via a cyclic bis[allene].

2. Progress toward a Convergent, Asymmetric Synthesis of Jervine.

3. Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

4. Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenation.

5. Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A.

Review 6. The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition.

7. Crystal structure of 5-(4-tert-but-oxy-phen-yl)-3-(4-n-octyloxyphen-yl)-4,5-di-hydro-isoxazole.

8. Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.