A simple and effective method for the reduction of acyl substituted heterocyclic 1,3-dicarbonyl compounds to alkyl derivatives by zinc - acetic acid - hydrochloric acid

Kappe, Thomas; Aigner, Rudolf; Roschger, Peter; Schnell, Barbara; Stadibauer, Wolfgang

doi:10.1016/0040-4020(95)00733-o

Cited by 19 publications

(9 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Therefore, we continued to optimize this reaction. Encouraged by Kappe's remarkable work, 25 by using zinc powder (particle size < 45 μm) in acetic acid/hydrochloric acid, ketone 12 was successfully reduced to desired product 9 , which was subsequently subjected to DMP oxidation without further chromatographic purifications, affording aldehyde 17 in 54% yield for two steps. Finally, the Wittig olefination was employed to provide the targeted (1 S ,2 S ,4 S )-β-elemene ( 3 ) in 82% yield, completing a five-step asymmetric total synthesis of 3 in 15.5% overall yield.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric total synthesis of (1S,2S,4S)-β-elemene

Chen

Feng²,

Liu

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Asymmetric total synthesis of (1S,2S,4S)-β-elemene

Chen

Feng²,

Liu

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…3-Ethyl-4-hydroxy-6-methyl-2 H -pyran-2-one was prepared from dehydroacetic acid (Sigma) as previously described. 33 …”

Section: Methodsmentioning

confidence: 99%

“…3-Ethyl-4-hydroxy-6-methyl-2H-pyran-2-one was prepared from dehydroacetic acid (Sigma) as previously described. 33 Bacterial Strains and Protein Purification. E. coli BL21(DE3) strains transformed with either pDHS9758, pDHS10019, and pSG3045, containing Sco2389 (acyl carrier protein, AcpP), Sco7221 (germicidin synthase, Gcs), and Sco4744 (acyl carrier protein synthase, AcpS), respectively, were constructed as previously described.…”

Section: ■ Experimental Proceduresmentioning

confidence: 99%

Biochemical and Structural Characterization of Germicidin Synthase: Analysis of a Type III Polyketide Synthase That Employs Acyl-ACP as a Starter Unit Donor

Chemler

Buchholz²,

Geders

et al. 2012

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Germicidin synthase (Gcs) from Streptomyces coelicolor is a type III polyketide synthase (PKS) with broad substrate flexibility for acyl groups linked through a thioester bond to either coenzyme A (CoA) or acyl carrier protein (ACP). Germicidin synthesis was reconstituted in vitro by coupling Gcs with fatty acid biosynthesis. Since Gcs has broad substrate flexibility, we directly compared the kinetic properties of Gcs with both acyl-ACP and acyl-CoA. The catalytic efficiency of Gcs for acyl-ACP was 10-fold higher than for acyl-CoA, suggesting a strong preference toward carrier protein starter unit transfer. The 2.9 Å germicidin synthase crystal structure revealed canonical type III PKS architecture along with an unusual helical bundle of unknown function that appears to extend the dimerization interface. A pair of arginine residues adjacent to the active site affect catalytic activity but not ACP binding. This investigation provides new and surprising information about the interactions between type III PKSs and ACPs that will facilitate the construction of engineered systems for production of novel polyketides.

show abstract

“…Kappe and coworkers have reported that a simple and effective method for the reduction of 1 to 3-ethyl-4-hydroxycoumarin 15 was achieved by using zinc powder in acetic acid/ hydrochloric acid as the reducing agent (Kappe et al, 1995) (Scheme 10).…”

Section: Reduction Reactionmentioning

confidence: 99%

3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications

Abdou

2017

Arabian Journal of Chemistry

View full text Add to dashboard Cite

The chemistry of 3-acetyl-4-hydroxycoumarin has gained increased interest in both synthetic organic and biological fields, since a large number of developments in the use of such compound seem to be of considerable value. This review summarizes results from the literature concerning the synthesis and reactions of 3-acetyl-4-hydroxycoumarin as well as its applications are also discussed.ª 2014 Production and hosting by Elsevier B.V. on behalf of King Saud University.

show abstract

A simple and effective method for the reduction of acyl substituted heterocyclic 1,3-dicarbonyl compounds to alkyl derivatives by zinc - acetic acid - hydrochloric acid

Cited by 19 publications

References 31 publications

Asymmetric total synthesis of (1S,2S,4S)-β-elemene

Asymmetric total synthesis of (1S,2S,4S)-β-elemene

Biochemical and Structural Characterization of Germicidin Synthase: Analysis of a Type III Polyketide Synthase That Employs Acyl-ACP as a Starter Unit Donor

3-Acetyl-4-hydroxycoumarin: Synthesis, reactions and applications

Contact Info

Product

Resources

About