Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4-pentanediol via lipase catalysed acylation

Lindström, Mona; Hedenström, Erik; Bouilly, Sandrine; Velonia, Kelly; Smonou, Ioulia

doi:10.1016/j.tetasy.2005.01.043

Cited by 8 publications

(3 citation statements)

References 33 publications

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“…Another example of the use of angelica lactones as precursors for biologically active compounds is the synthesis of pine sawfly sex pheromones by the Smonou group (Scheme ) . In this work, the authors report the initial base‐catalyzed isomerization of α‐AL to β‐AL followed by the 1,4‐conjugate addition of organocuprates to obtain lactone intermediate 23 .…”

Section: Synthetic Applications Of Angelica Lactonesmentioning

confidence: 99%

“…[48] Another example of the use of angelica lactones as precursors for biologically active compounds is the synthesis of pine sawfly sex pheromones by the Smonou group (Scheme 23). [49] In this work, the authors report the initial base-catalyzed isomerization of a-AL to b-AL followed by the 1,4-conjugatea ddi-Scheme19. a-ALa st he starting material for the synthesis of cyclic carbinol amides, as intermediates in the synthesis of a cis-jasmone precursor.…”

Section: Applications Of Angelica Lactones As Building Blocks In Orgamentioning

confidence: 99%

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Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

et al. 2017

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The upgrading of biomass‐derived compounds has arisen in recent years as a very promising research field in both academia and industry. In this sense, a lot of new processes and products have been developed, often involving levulinic acid as a starting material or intermediate. In the last few years, though, other scaffolds have been receiving growing attention, especially, angelica lactones. Considering these facts and the emergent applications of said molecules, in this review we will discuss their preparation and applications; the use of these frameworks as starting materials in organic synthesis to produce potential bioactive compounds will be covered, as will their use as a foundation to highly regarded compounds such as liquid alkanes with prospective use as fuels and polymers.

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Section: Synthetic Applications Of Angelica Lactonesmentioning

confidence: 99%

Section: Applications Of Angelica Lactones As Building Blocks In Orgamentioning

confidence: 99%

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

et al. 2017

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“…[2] These important achievements encourage chemists to seek more innovative ways to leverage LA to synthesize highly value-added chemicals. Amongt hen, a-AL, which is readily available from LA by intramolecular dehydration, has attracted extensive attention [3][4][5][6] as ab utenolidev ariant because of its potentiali n the construction of g-substituted butenolides, [7] naturalp roducts, and biologically active molecules (Figure 1). Various types of reactions were reported by using a-AL as nucleophile, such as Michael addition, Morita-Baylis-Hillman, [5f] and Pd-catalyzed cross-coupling reactions.…”

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confidence: 99%

Regioselective β‐Arylation of α‐Angelica Lactone through Isomerization/Addition under Mild Conditions

Zhuo

Gong

et al. 2020

ChemSusChem

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The conversion of biomass‐based platform molecules into various high‐value chemicals greatly promotes the utilization of renewable biomass resources. Herein, an example of Rh‐catalyzed β‐arylation of levulinic‐acid‐derived α‐angelica lactone was reported, providing the γ‐lactone‐structure products with high regioselectivity. Both arylboronic and alkenylboronic acids could be applied in this transformation. This reaction tolerated a variety of synthetically important functional groups. Moreover, the obtained γ‐lactone products could be readily converted to high‐value products such as 1,4‐diols and γ‐methoxy‐carboxylates.

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Resolution of Alcohols

Larock

Worlikar

2018

Comprehensive Organic Transformations

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Deracemization Resolution of Alcohols by Lipase‐Catalyzed Esterification Resolution of Alcohols by Lipase‐Catalyzed Transesterification Resolution of Alcohols by Esterase‐Catalyzed Esterification Resolution of Alcohols by Protease‐Catalyzed Esterification Resolution of Alcohols by Immobilized Morchella esculenta ‐Catalyzed Transesterification Resolution of Alcohols by Acylase‐Catalyzed Transesterification Resolution of Alcohols by Hydrolysis of Esters or Carbonates Resolution of Alcohols and Phenols by Alcoholysis Resolution of Alcohols by Aminolysis of Esters Dynamic Kinetic Resolution of Alcohols Mediated by Lipase and Metal Catalysis Resolution of Alcohols by Nonenzymatic Acylation Resolution of Alcohols by Oxidation Resolution of Allylic Alcohols Resolution of Haloalcohols Resolution of 2,3‐Epoxy Alcohols Resolution of Alcohols by Formation of an SiO Bond Resolution of Alcohols by Dehydration of β‐Hydroxy Esters Resolution of Aldols by a retro ‐Aldol Reaction Resolution of 2‐Nitro Alcohols by CC Bond Cleavage Resolution of tert ‐Cyclobutanols by Pd‐Catalyzed CC Bond Cleavage Resolution of Secondary Alcohols by a Chiral Heteroatom Auxiliary Resolution of Diols and Triols Resolution of Alcohols by Preferential Crystallization Resolution of Alcohols by Supramolecular Crystallization Resolution of Alcohols by Sublimation

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Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4-pentanediol via lipase catalysed acylation

Cited by 8 publications

References 33 publications

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

Regioselective β‐Arylation of α‐Angelica Lactone through Isomerization/Addition under Mild Conditions

Resolution of Alcohols

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