Vitamins, 5. Vitamin K

Netscher, Thomas; Bonrath, Werner; Bendik, Igor; Zimmermann, Peter‐Jan; Weber, F.; Rüttimann, August

doi:10.1002/14356007.o27_o08.pub2

Cited by 4 publications

(4 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our first application focused on α-allylations ultimately leading to both MK-7 and MK-9. These couplings were predicated on the original route championed by Ruttiman, 21 who devised a clever Diels–Alder/retro-Diels–Alder scheme. Using 2-methylnaphthoquinone, readily obtained via oxidation of 2-methylnaphthalene, 22 Diels–Alder (DA) addition of cyclopentadiene (Cp) leads to adduct 32 which is perfectly situated for subsequent monoallylation (Scheme 5).…”

Section: Resultsmentioning

confidence: 99%

“…Using 2-methylnaphthoquinone, readily obtained via oxidation of 2-methylnaphthalene, 22 Diels–Alder (DA) addition of cyclopentadiene (Cp) leads to adduct 32 which is perfectly situated for subsequent monoallylation (Scheme 5). In the originally described procedure, 21 diketone adduct 32 was treated with base and phytyl bromide to give vitamin K 1 . By contrast, using the same precursor to MK-7, neat α-allylation afforded 33 with a reaction time of 60 minutes.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Allylations of aryl/heteroaryl ketones: neat, clean, and sustainable. Applications to targets in the pharma- and nutraceutical industries

Wood

Lee

et al. 2022

Green Chem.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Allylations of aryl/heteroaryl ketones: neat, clean, and sustainable. Applications to targets in the pharma- and nutraceutical industries

Wood

Lee

et al. 2022

Green Chem.

View full text Add to dashboard Cite

show abstract

“…An industrial chemical process, starting from the oxidation of 2-methylnaphthalin via the alkylation of menadiol in the 3-position by isophytol, has been implemented. Challenges such as insufficient selectivity of the alkylation step have been overcome by research groups at Roche and Merck KGaA by using monoacylated menadiol [80,81]. As the biosynthesis of vitamin K1, also designated as phylloquinone, is known [82], a potential alternative biotechnological approach for manufacturing vitamin K1 is of much interest [83].…”

Section: Vitamin K1mentioning

confidence: 99%

Biocatalysis in the Swiss Manufacturing Environment

et al. 2020

View full text Add to dashboard Cite

Biocatalysis has undergone a remarkable transition in the last two decades, from being considered a niche technology to playing a much more relevant role in organic synthesis today. Advances in molecular biology and bioinformatics, and the decreasing costs for gene synthesis and sequencing contribute to the growing success of engineered biocatalysts in industrial applications [1]. However, the incorporation of biocatalytic process steps in new or established manufacturing routes is not always straightforward. To realize the full synthetic potential of biocatalysis for the sustainable manufacture of chemical building blocks, it is therefore important to regularly analyze the success factors and existing hurdles for the implementation of enzymes in large scale small molecule synthesis. Building on our previous analysis of biocatalysis in the Swiss manufacturing environment [2], we present a follow-up study on how the industrial biocatalysis situation in Switzerland has evolved in the last four years. Considering the current industrial landscape, we record recent advances in biocatalysis in Switzerland as well as give suggestions where enzymatic transformations may be valuably employed to address some of the societal challenges we face today, particularly in the context of the current Coronavirus disease 2019 (COVID-19) pandemic.

show abstract

“…The chemical synthesis of polyprenols has been the subject of numerous studies for a long time. 12,[19][20][21][22][23][24][25][26] However, most if not all, of these methods are multistep, very time-consuming and frequently require low and high temperatures or toxic chemicals. This makes synthesis, especially in a non-specialized laboratory, difficult and discouraging.…”

Section: Introductionmentioning

confidence: 99%