- Total Synthesis of an Isatis indigotica-Derived Alkaloid Using a Biomimetic Thio-Diels-Alder Reaction
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A biomimetic thio-Diels-Alder reaction between a dienylthiadiazole and 3-thioisatin leads to the Isatis indigotica-derived alkaloid (1), along with its diastereomer 2. This synthetic study, supported by molecular modeling, establishes the viability of the proposed biosynthesis by thio-Diels-Alder cycloaddition, a very rare reaction in nature. Moreover, the results described infer that the diastereomer 2 is an as-yet undiscovered natural product present in Isatis indigotica.
- Davison, Emma K.,Hume, Paul A.,Sperry, Jonathan
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supporting information
p. 3545 - 3548
(2018/06/26)
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- MICROORGANISMS FOR PRODUCING 4C-5C COMPOUNDS WITH UNSATURATION AND METHODS RELATED THERETO
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The invention provides a non-naturally occurring microbial organism having a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol, pathway. The microbial organism contains at least one exogenous nucleic acid encoding an enzyme in a pathway. The invention additionally provides a method for producing butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol,. The method can include culturing a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol-producing microbial organism, where the microbial organism expresses at least one exogenous nucleic acid encoding a pathway enzyme in a sufficient amount, and under conditions and for a sufficient period of time to produce butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol.
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- New and concise syntheses of the bicyclic oxamazin core using an intramolecular nitroso diels-alder reaction and ring-closing olefin metathesis
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Herein two new and concise synthetic approaches for making an unsaturated bicyclic oxamazin core are reported. The first involves the use of an intramolecular Diels-Alder reaction to form both of the fused rings in one step. The second approach incorporates ring-closing olefin metathesis in the final step to form the second fused ring of the core. The scope of the second approach was also expanded further to afford larger ringed bicyclic systems.
- Watson, Kyle D.,Carosso, Serena,Miller, Marvin J.
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p. 358 - 361
(2013/03/13)
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- De-novo Synthesis of Enantiomerically Pure Deoxy- and Aminodeoxyfuranosides
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(R)-3-Hydroxy-4-pentenoic acid (2), readily available by an aldol addition of doubly deprotonated (R)-2-hydroxy-1,2,2-triphenylethyl acetate (1) to acrolein, functions as a key intermediate for the synthesis of enantiomerically pure deoxy- and aminodeoxyf
- Graef, Silke,Braun, Manfred
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p. 1091 - 1098
(2007/10/02)
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- SYNTHESIS OF UNSATURATED HYDROXY ACIDS BY THE COBALT CARBONYL AND PHASE TRANSFER CATALYZED CARBONYLATION OF VINYL EPOXIDES
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Phase transfer catalyzed reaction of vinyl epoxides with carbon monoxide, methyl iodide, catalytic amounts of cobalt carbonyl and TDA-1, affords β-hydroxy acids.High regioselectivity was observed in some cases.
- Alper, Howard,Calet, Serge
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p. 1763 - 1766
(2007/10/02)
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- Stereoselectivity of Electrophile-Promoted Cyclizations of γ-Hydroxyalkenes. An Investigation of Carbohydrate-Derived and Model Substrates
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We have investigated cyclization reactions of γ-hydroxyalkenes bearing an alkoxy or alkyl substituent on the allylic carbon.A variety of electrophiles N-bromosuccinimide, N-iodosuccinimide, iodine, mercury(II) acetate, mercury(II) trifluoroacetate, mercu
- Reitz, Allen B.,Nortey, Samuel O.,Maryanoff, Bruce E.,Liotta, Dennis,Robert, Monahan
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p. 4191 - 4202
(2007/10/02)
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- STEREOSELECTIVE IODOLACTONIZATION OF ACYCLIC UNSATURATED 3-HYDROXYACIDS
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A stereoselective method for preparing 3-hydroxy-4-alkyl-γ-lactones is reported.Iodolactonization of 3-hydroxy-4-alkenoic acids produces predominantly the thermodynamically less stable 3,4-cis products, which undergo methanolysis to threo-epoxyalcohols.
- Chamberlin, A. Richard,Dezube, Milana,Dussault, Patrick
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p. 4611 - 4614
(2007/10/02)
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