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Bonini et al., 1992 - Google Patents

Enzyme catalysed lactonization of 3, 5 dihydroxy esters: Enantioselective synthesis of naturally occurring 3-hydroxy-5-decanolide,(−)-massoialactone, and 3-hydroxy …

Bonini et al., 1992

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Document ID
8300722296935654818
Author
Bonini C
Pucci P
Racioppi R
Viggiani L
Publication year
Publication venue
Tetrahedron: Asymmetry

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Abstract Synthesis of optically active (+)-3-hydroxy-5-decanolide,(−)-massoialactone and of the recently isolated 3-hydroxy-5-icosanolide was achieved by enzyme-catalysed lactonization of racemic 3, 5 dihydroxy esters with PPL in dry Et 2 O. Ees vary from 86% up …
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    • C—CHEMISTRY; METALLURGY
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    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
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    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atom
    • C12P17/06—Oxygen as only ring hetero atom containing a six-membered hetero ring, e.g. fluorescein
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    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atom
    • C12P17/04—Oxygen as only ring hetero atom containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
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    • C12P7/00—Preparation of oxygen-containing organic compounds
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    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
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    • C12P7/00—Preparation of oxygen-containing organic compounds
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    • C12P17/10—Nitrogen as only ring hetero atom
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