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Literature DB >> 16699591

Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.

Pilho Kim¹, Clifton E Barry, Cynthia S Dowd.

Abstract

Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of desired product to deformylated product.

Entities: Chemical

Year: 2006 PMID： 16699591 PMCID： PMC1450324 DOI： 10.1016/j.tetlet.2006.03.058

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

27 in total

1. Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure.

Authors: K C Nicolaou; Scott A Snyder; Xianhai Huang; Klaus B Simonsen; Alexandros E Koumbis; Antony Bigot
Journal: J Am Chem Soc Date: 2004-08-18 Impact factor: 15.419

2. The synthesis of (-)-isodomoic acid C.

Authors: Jonathan Clayden; Faye E Knowles; Ian R Baldwin
Journal: J Am Chem Soc Date: 2005-03-02 Impact factor: 15.419

3. Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis.

Authors: L Kremer; J D Douglas; A R Baulard; C Morehouse; M R Guy; D Alland; L G Dover; J H Lakey; W R Jacobs; P J Brennan; D E Minnikin; G S Besra
Journal: J Biol Chem Date: 2000-06-02 Impact factor: 5.157

Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.

1. Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure.

2. The synthesis of (-)-isodomoic acid C.

3. Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis.

4. Inhibition of beta-ketoacyl-acyl carrier protein synthases by thiolactomycin and cerulenin. Structure and mechanism.

5. Domino reactions that combine an azido-Schmidt ring expansion with the Diels-Alder reaction.

6. Antimycobacterial action of thiolactomycin: an inhibitor of fatty acid and mycolic acid synthesis.

7. Thiolactomycin, a new antibiotic. IV. Biological properties and chemotherapeutic activity in mice.

8. Effect of thiolactomycin on the individual enzymes of the fatty acid synthase system in Escherichia coli.

9. Mechanism of action of the antibiotic thiolactomycin inhibition of fatty acid synthesis of Escherichia coli.

10. Synthesis of the carbocyclic core of the cornexistins by ring-closing metathesis.

Review 1. Recent advances in the chemistry and biology of naturally occurring antibiotics.

2. Synthesis, bioactivity, and enzymatic modification of antibacterial thiotetromycin derivatives.

3. Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity.