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- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/06%3A_Amino_Acids_and_Alkaloids/6.09%3A_Study_Questions
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/01%3A_Some_Principles_of_Synthetic_Planning
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/06%3A_Amino_Acids_and_Alkaloids/6.06%3A_Biosynthesis_of_Nonaromatic_Amino_AcidsTransamination is then completed by the reaction of an α-keto acid with 411 to produce the corresponding α-amino acid and regenerate pyridoxal by a process that is analogous to the reverse of the reac...Transamination is then completed by the reaction of an α-keto acid with 411 to produce the corresponding α-amino acid and regenerate pyridoxal by a process that is analogous to the reverse of the reaction that generates 411 plus α-keto glutarate from 407 plus glutamic acid.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/01%3A_Some_Principles_of_Synthetic_Planning/1.01%3A_IntroductionFurthermore, the target will generally be shown to the left of the ⇒ symbol and the precursor(s) to the right.The dislocation may correspond to a single known chemical reaction, or a hypothetical reac...Furthermore, the target will generally be shown to the left of the ⇒ symbol and the precursor(s) to the right.The dislocation may correspond to a single known chemical reaction, or a hypothetical reaction, or may be the result of a multistep retrosynthetic process. An important feature of the discussion is the inclusion of unsuccessful plans that emerged from the work of leading practitioners of the art and science of organic total synthesis.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/03%3A_Fatty_Acids_and_Prostaglandins/3.06%3A_Enantioselective_Syntheses_of_ProstaglandinsThe abundant functional (oxygen on every carbon) and stereochemical information present in sugars suggests an even more ambitious synthesis of prostaglandins: incorporation of several sugar-related ce...The abundant functional (oxygen on every carbon) and stereochemical information present in sugars suggests an even more ambitious synthesis of prostaglandins: incorporation of several sugar-related centers of chirality from a sugar starting material with a sugar-related hydroxyl at the incipient 10 position of PGF 2α . Thus, polar disconnection of PGF 2α with the boundary condition of uncovering a sugar-derived homochiral segment suggests a precursor 274 in which the target related polar reacti…
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/05%3A_Polyketides/5.01%3A_Orselenic_AcidFormation of the intermediate polyacetyl or propionyl chains in the biosynthesis of polyketides is closely related to fatty acid biosynthesis. A total synthesis of orselenic acid was achieved by a bio...Formation of the intermediate polyacetyl or propionyl chains in the biosynthesis of polyketides is closely related to fatty acid biosynthesis. A total synthesis of orselenic acid was achieved by a biomimetic strategy, that is, by a strategy that mimics the biosynthesis of this acetogenin. 1 Thus, the trianion of 2,4,6-heptanetrione was carboxylated to yield 3,5,7-triketo octanoic acid (1) that readily underwent intramolecular aldol condensation and dehydration to give orselenic acid (2).
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/04%3A_Terpenes/4.01%3A_Biosynthesis_of_Monoterpenes-_LoganinTerpenes have a large variety of carbon skeletons characterized by branched chains, and often complex multicyclic ring systems. They are oligomers of the biological isoprene unit, which is a relativel...Terpenes have a large variety of carbon skeletons characterized by branched chains, and often complex multicyclic ring systems. They are oligomers of the biological isoprene unit, which is a relatively reduced hydrocarbon comprised of five carbons. It is produced in nature from three molecules of a relatively oxidized two carbon starting material, acetic acid in the form of acetyl CoA.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/01%3A_Some_Principles_of_Synthetic_Planning/1.03%3A_Perception_of_Structure-Functionality_RelationshipsIt is useful to define the functionality level 9 of an atom as f = the number of valence electrons in the neutral atom minus the number of electrons assigned to the atom by the following protocol: all...It is useful to define the functionality level 9 of an atom as f = the number of valence electrons in the neutral atom minus the number of electrons assigned to the atom by the following protocol: all bonding electrons are divided equally between C-C, C=C, C≡C, C-H, M-M or X-X, but all bonding electrons are given to the better nucleofuge (often but not always the more electronegative atom, vide infra) for C-X, C-M, or X-Y bonds, where X and Y are hetero atoms, and M is a metal.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/05%3A_Polyketides/5.04%3A_Erythronolide_BGeneration of only 1 of the 2048 possible diastereomers of the acyclic intermediate 87 is the remarkable consequence of the asymmetry of the homochiral catalysts (enzymes) that promote the condensatio...Generation of only 1 of the 2048 possible diastereomers of the acyclic intermediate 87 is the remarkable consequence of the asymmetry of the homochiral catalysts (enzymes) that promote the condensations and reductions responsible for producing ten asymmetric centers.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/02%3A_Sugars_-_Biosynthetic_Starting_Materials/2.01%3A_Carbon_Fixation-_Biosynthesis_of_SugarsThis is step #1 in the biosynthesis of all natural products. (2) RuBP serves as a catalyst in a cycle that converts six CO2 into one molecule of glucose. (3) The RuBP consumed in step #1 is r...This is step #1 in the biosynthesis of all natural products. (2) RuBP serves as a catalyst in a cycle that converts six CO2 into one molecule of glucose. (3) The RuBP consumed in step #1 is regenerated by a series of reactions, that reshuffle the atoms of ten molecules of the three-carbon sugar G3P into six molecules of the five- carbon RuBP. (4) All C-C bond formation and cleavage involves condensations (aldol, Claisen, benzoin) that are readily reversible.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Complex_Molecular_Synthesis_(Salomon)/02%3A_Sugars_-_Biosynthetic_Starting_Materials/2.02%3A_Synthesis_of_SugarsOne hypothesis is that the formation of glycolaldehyde from two molecules of formaldehyde involves proton abstraction to generate a tiny concentration of acylcarbanion that condenses with a second mol...One hypothesis is that the formation of glycolaldehyde from two molecules of formaldehyde involves proton abstraction to generate a tiny concentration of acylcarbanion that condenses with a second molecule of formaldehyde. An aldol condensation strategy for the C-C connective synthesis of ribulose is suggested by the latent nucleophilicity of the α-carbon enabled by the carbonyl group of dihydroxyacetone to react with a glycolaldehyde electrophile.
