Baker’s yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal

Fuganti, Claudio; Serra, Stefano; Dulio, Andrea

doi:10.1039/a808772e

Cited by 74 publications

(34 citation statements)

References 18 publications

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“…The use of baker's yeast in the reductive bioconversion of several chiral intermediates for the enantioselective synthesis of bisabolane sesquiterpenes was well‐established by Fuganti and co‐workers 42–44. The enantioselective preparation of ( S )‐(+)‐3‐( p ‐tolyl)butan‐1‐ol by baker's yeast reduction of ( E )‐3‐( p ‐tolyl)but‐2‐en‐1‐ol was demonstrated44.…”

Section: Reductive Biotransformation Of Sesquiterpenoids Using S Cermentioning

confidence: 99%

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Khor

Uzir

2010

Yeast

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Terpenes and terpenoids are among the key impact substances in the food and fragrance industries. Equipped with pharmacological properties and applications as ideal precursors for the biotechnological production of natural aroma chemicals, interests in these compounds have been escalating. Hence, the syntheses of new derivatives that can show improved properties are often called for. Stereoselective biotransformation offers several benefits to increase the rate of production, in terms of both the percentage yield and its enantiomeric excesses. Baker's yeast (Saccharomyces cerevisiae) is broadly used as a whole cell stereospecific reduction biocatalyst, due to its capability in reducing carbonyls and carbon-carbon double bonds, which also extends its functionality as a versatile biocatalyst in terpenoid biotransformation. This review provides some insights on the development and prospects in the reductive biotransformation of monoterpenoids and sesquiterpenoids using S. cerevisiae, with an overview of strategies to overcome the common challenges in large-scale implementation.

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Section: Reductive Biotransformation Of Sesquiterpenoids Using S Cermentioning

confidence: 99%

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Khor

Uzir

2010

Yeast

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“…1 and t 2 are the retention times in minutes for the two enantiomers of compounds 1-4, respectively on GC-column b-dex 120.…”

mentioning

confidence: 99%

Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol

Sabbani

Hedenström

Andersson

2007

Tetrahedron: Asymmetry

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“…4 The alcohol was converted to the carbonate by reaction with methyl chloroformate in pyridine (80%). The stereochemical assignment was made by comparison with (S)-(+)-3-(p-tolyl)butanal {[α] D + 39.6 (c1, CHCl 3 )} synthesized by Dulio et al 7 The observed aldehyde stereochemistry (R) is consistent with the expected mechanism which involves inversion of configuration during π -allyl formation and retention during transmetallation and reductive elimination (i.e., overall retention). The use of trifurylphosphine was critical in this reaction.…”

Section: Resultsmentioning

confidence: 84%

Palladium Catalyzed Additions to Allylic Hydroxy Phosphonates: Applications in the Enantioselective Synthesis of Enterolactone and Turmerone

Rowe

Scholten

Spilling

2002

Phosphorus, Sulfur, and Silicon and the Related Elements

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Reaction of nonracemic allylic hydroxy phosphonates, prepared by the asymmetric phosphonylation of unsaturated aldehydes, with methyl chloroformate in pyridine yields the corresponding carbonates. The carbonates are excellent substrates for the palladium-catalyzed addition of nucleophiles. Addition of the nucleophile is highly regioselective, resulting in γ -substituted vinyl phosphonates. The reaction of the allylic carbonates with aryl stannanes and malonates has been investigated. Progress in the application of these reactions to the synthesis of turmerone and enterolactone is reported.

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Baker’s yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal

Cited by 74 publications

References 18 publications

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Saccharomyces cerevisiae: a potential stereospecific reduction tool for biotransformation of mono‐ and sesquiterpenoids

Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol

Palladium Catalyzed Additions to Allylic Hydroxy Phosphonates: Applications in the Enantioselective Synthesis of Enterolactone and Turmerone

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