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Literature DB >> 34846908

Stereoselective Synthesis of the Spirocyclic γ-Lactam Core of the Ansalactams.

Zhanhao Liang^1,2, You-Chen Lin^1,2, Joshua G Pierce^1,2.

Abstract

Ansalactam A is an ansa macrolide natural product that contains a densely functionalized spiro-γ-lactam core containing three contiguous stereocenters. This unusual motif distinguishes it from other members of this family and represents a significant synthetic challenge. Herein, we report the development of a stereoselective formal [3+2] cycloaddition reaction for the construction of this key spiro-γ-lactam motif for the first time, thereby enabling access to the northern domain of ansalactam A.

Entities: Chemical

Mesh：
Spiro Compounds

Substances：
Spiro Compounds

Year: 2021 PMID： 34846908 PMCID： PMC9437948 DOI： 10.1021/acs.orglett.1c03782

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.072

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References

9 in total

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Stereoselective Synthesis of the Spirocyclic γ-Lactam Core of the Ansalactams.

Review 1. Rifamycin-mode of action, resistance, and biosynthesis.

2. Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway.

3. Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P₁ and S1P₅ Selective Agonist for the Treatment of Autoimmune Diseases.

4. Structure and biosynthesis of the marine streptomycete ansamycin ansalactam A and its distinctive branched chain polyketide extender unit.

5. Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs).

Review 6. Geldanamycin and its anti-cancer activities.

7. Leveraging Marine Natural Products as a Platform to Tackle Bacterial Resistance and Persistence.

Review 8. The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition.

9. Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

Stereoselective Synthesis of the Spirocyclic γ-Lactam Core of the Ansalactams.

Review 1. Rifamycin-mode of action, resistance, and biosynthesis.

2. Ansalactams B-D Illustrate Further Biosynthetic Plasticity within the Ansamycin Pathway.

3. Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P1 and S1P5 Selective Agonist for the Treatment of Autoimmune Diseases.

4. Structure and biosynthesis of the marine streptomycete ansamycin ansalactam A and its distinctive branched chain polyketide extender unit.

5. Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs).

Review 6. Geldanamycin and its anti-cancer activities.

7. Leveraging Marine Natural Products as a Platform to Tackle Bacterial Resistance and Persistence.

Review 8. The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition.

9. Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

3. Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P₁ and S1P₅ Selective Agonist for the Treatment of Autoimmune Diseases.