[最新] α β-γ δ-unsaturated-γ-lactone 220731

Bislatumlides AF (16) represent the only biscembranoids formed by the undescribed coupling pattern of DielsAlder cycloaddition between the Δ(1(2)) double bond involving an α,βunsaturated γlactone ring as a dienophile group and a trisubstituted conjugated Δ(21(34))/Δ(35(36))butadiene moietyLactones that occur naturally are primarily saturated and unsaturated γ and δlactones, but to a lesser extent, macrocyclic lactones The γlactones and δlactones are intramolecular esters of the related hydroxy fatty acids They provide the aromaThe stereoselective synthesis of the cisγ,δdisubstituted α,βunsaturated δlactone fragment of the leustroducsins or phoslactomycins was accomplishedThe new synthetic strategy involves a catalytic asymmetric ketene–aldehyde 22 cycloaddition leading to the formation of a cisdisubstituted βlactoneRing extension by enolate condensation and

Synthetic Approaches To A B Unsaturated D Lactones And Lactols Boucard 07 European Journal Of Organic Chemistry Wiley Online Library

α β-γ δ-unsaturated-γ-lactone

α β-γ δ-unsaturated-γ-lactone-Ringclosing olefin metathesis of acrylates derived from allylic and homo allylic alcohols in the presence of the Grubbs' catalyst (1015 mol%) and titanium isopropoxide (033 equiv) provided ready access to α, βunsaturated γ and δlactones and anDiversely Substituted SugarLinked α,βUnsaturated γLactones from SugarDerived Baylis−Hillman Adducts via a RCM Journal of Combinatorial Chemistry 07 , 9 (1) , 6269

B G Unsaturated A Amino Acid D Lactones Precursors For Polyhydroxy Amino Acids Sciencedirect

Field of δalkylatedγsilylatedα,βunsaturated δlactones 1 These compounds are easily synthesized in enantiomerically pure forms and in a highly diastereoselective manner by a tandem rearrrangement / alkylationlactonization sequence starting from α,βepoxyγ,δvinylsilanes 22 (Scheme 1) TBDMS O CO2Me 1) Pd(0) 2) RM O O R TBDMSConjugate additions to 6substituted α,βunsaturated δlactones have been little studied As opposed to the γlactone counterparts, addition of benzylamine or Nbenzylhydroxylamine to these δlactones yields products from attack at the carbonyl However, switching to Obenzylhydroxylamine produces the conjugate adduct 31Up to10%cash backMagnesium in methanol is an effective reagent for the selective reduction of α,βunsaturated γ and δlactones for getting saturated derivatives of these compounds in high to excellent yields Other reducible functionalities such as CO 2 Et and CN remain unaffected It is known that many representatives of saturated γlactones have

α,βUnsaturated γlactones occur widely in nature and appear throughout the plant kingdom from the simple metabolites of lichens and fungi 1 to the sesquiterpenes 2 and the steroidal glycosides 3 They have also been described in animal species such as sponges,4, 4(a), 4(b), 4(c), 4(d), 4(e), 4(f) butterflies 5 and insects, 6 playingα,βUnsaturated γ and δlactones were selectivity reduced to the corresponding saturated lactones and oxospiro systems respectively using sodium borohydride in the presence of triethylamine in THF, in excellent yields Keywords Conjugate reduction, α,βunsaturated lactones, sodium borohydride, spiro lactones IntroductionThe γlactones γoctalactone, γnonalactone, γdecalactone, γundecalactone can be prepared in good yield in a onestep process by radical addition of primary fatty alcohols to acrylic acid, using ditertbutyl peroxide as a catalyst Reactions The most stable structure for lactones are the 5membered γlactones and 6membered δlactones because, as in all organic cycles, 5 and 6

Three new arylalkenyl α,βunsaturated δlactones, cryptobrachytones AC (13), together with one known analogue kurzilactone (4), were isolated from the leaves and twigs of Cryptocarya brachythyrsa Their structures were elucidated based on extensive spectroscopic data and electronic circular dichroism (ECD) analysis All the isolates were evaluated in vitro for antiSemantic Scholar extracted view of The βlactone route to α, βunsaturated δlactones Total syntheses of (′)goniothalamin and ()massoialactone by L Fournier et alTwo novel α,βunsaturated γlactonohydrazides, geralcin A (2) and geralcin B (3), were isolated from Streptomyces sp LMA545 This unusual scaffold consists of the condensation of alkylhydrazide with an α,βunsaturated γlactone, 3 (5oxo2Hfuran4yl)propanoic acid (1), which was isolated from the same broth culture

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Synthetic Approaches To A B Unsaturated D Lactones And Lactols Boucard 07 European Journal Of Organic Chemistry Wiley Online Library

A coppercatalyzed cascade reaction of α,βunsaturated esters with keto esters is reported It features a coppercatalyzed reductive aldolization followed by a lactonization This method provides a facile approach to prepare γcarboxymethylγlactones and δcarboxymethylδlactones under mild reaction conditions

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Synthetic Approaches To A B Unsaturated D Lactones And Lactols Boucard 07 European Journal Of Organic Chemistry Wiley Online Library

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Novel Photoadditions Of Tertiary Amines To The A Position Of A B Unsaturated G D Epoxy Nitriles Journal Of The Chemical Society Perkin Transactions 1 Rsc Publishing

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The Potential Of B Hydroxy G Vinyl G Lactone In The Synthesis Of Natural Products And Beyond Fernandes European Journal Of Organic Chemistry Wiley Online Library

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Total A B Unsaturated G Lactone Acetogenins In Annona Muricata By Proton Nmr Spectroscopy Springerlink

B G Unsaturated A Amino Acid D Lactones Precursors For Polyhydroxy Amino Acids Sciencedirect

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Mechanisms Of Chloro And Bromolactonization Of G D Unsaturated Download Scientific Diagram

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Synthetic Approaches To A B Unsaturated D Lactones And Lactols Boucard 07 European Journal Of Organic Chemistry Wiley Online Library

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Direct Lactonization Of A Amino G D Unsaturated Carboxylic Acid Esters Via Olefin Activation Stereo And Regioselective Production Of Homoserine Lactone Scaffolds Having Contiguous Stereocenters Sciencedirect