Showing papers on "Total synthesis published in 1989"
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01 Jan 1989
TL;DR: Asymmetric derivatization of glycine as mentioned in this paper has been shown to be a useful technique for the synthesis of complex amino acids. But it is difficult to verify its correctness.
Abstract: Asymmetric derivatization of glycine. Homologation of the beta-carbon. Electrophilic amination of enolates. Nucleophilic amination of alpha-substituted acids. Asymmetric Strecker syntheses. Asymmetric hydrogenation of dehydroamino acids. Enzymatic syntheses of alpha-amino acids. Miscellaneous methods. Total synthesis of complex amino acids. Author index. Subject index.
653 citations
TL;DR: La synthese de l'octahydro pentahydroxy-1,2,3,4,7 dioxolo- 1,3 [4,5] phenanthridinone-6 a ete effectuee; le controle stereochimique de la synthetse est realise par une serie de reactions de fonctionalisations cis vicinales.
Abstract: La synthese de l'octahydro pentahydroxy-1,2,3,4,7 dioxolo-1,3 [4,5-j] phenanthridinone-6 a ete effectuee; le controle stereochimique de la synthese est realise par une serie de reactions de fonctionalisations cis vicinales
153 citations
147 citations
124 citations
117 citations
TL;DR: In this paper, a fully protected palytoxin carboxylic acid was synthesized from eight building blocks using Ni(II)/Cr(II)-mediated coupling reaction.
Abstract: The total synthesis of a fully protected palytoxin carboxylic acid was achieved from eight building blocks. The C.22-C.23 and C.37-C.38 bonds were formed via Wittig olefination, followed by hydrogenation. The Ni(II)/Cr(II)-mediated coupling reaction was utilized for formation of the C.7-C.8 annd C.84-C.85 bonds. The TIOH-accelerated diene synthesis was applied for formation of the C.75-C.76 bond. The C.98-C.99 olefinic bond was introduced by a Wittig reaction, whereas the C.51-C.52 olefinic bond was introduced by a Horner-Emmons reaction, followed by stereoselective LiBH 4 /EuCl 3 reduction
108 citations
105 citations
99 citations
TL;DR: Synthetic (2 S, 3 R )-3-Amino-4-hydroxy-2-methylbutanoic acid, γ-lactone, and (4 S, 5 S )-2,4-dimethyl-5- methoxy-6-phenyl-2hexen-1-ol were oxidized and linked to give Adda as discussed by the authors.
97 citations
TL;DR: The first total synthesis of (±)-huperzine A, a new lycopodium alkaloid, was described in this paper, where the synthesis was carried out in the early 1990s.
93 citations
TL;DR: Preparation de ces composes a partir d'une oxime de cyclohexyl-2 propanal et d'un O-benzyl 2 fucose pour la pseudopterosine E ou d'unes bromure de xylopyranosyle.
Abstract: Preparation de ces composes a partir d'une oxime de cyclohexyl-2 propanal et d'un O-benzyl-2 fucose pour la pseudopterosine E ou d'une bromure de xylopyranosyle pour la pseudopterosine A
TL;DR: In this article, a highly convergent synthesis of the macrolide natural product milbemycin β1 is reported, which includes the introduction of the C11-C15 side chain by selective ring opening of a symmetrical 1,4-pentane bis-epoxide, followed by reaction with the anion derived from the 2,3-trans-dimethyl-6-phenylsulphonyl pyran.
TL;DR: The syntheses feature the use of camphanic acid esters for resolution of protected inositols, and theUse of tetrabenzylpyrophosphate as an efficient phosphorylating agent for polyhydroxy alcohols.
TL;DR: The reaction de cyclenes-2ones avec des bromocrotonates donne en une etape les vinylcyclopropanes corespondants. Application a la synthese de l'acide retigeranique as discussed by the authors
Abstract: La reaction de cyclenes-2ones avec des bromocrotonates donne en une etape les vinylcyclopropanes corespondants. Ces derniers subissent differentes transpositions et fournissent des derives pentaleno dioxole, des bicyclo [3.3.0] octene-1, des bicyclo [4.3.0] nonene-7, des bicyclo [5.3.0] decene-8 ― carboxylates d'ethyle. Application a la synthese de l'acide retigeranique
TL;DR: Tungsten hexacarbonyl or rhodium(II) acetate mediated reductive coupling of a dithiolane or 2,3-diphenyl-N-aziridinohydrazone with a regioselectively activated unsymmetrical dimethoxyphthalimide provides the key step in total synthesis of the isoindolobenzazepine alkaloid chilenine as discussed by the authors.
TL;DR: In this article, the synthese d'un derive de pyrrolo [1,8,8a-a] quinoleine precurseur d'alcaloides is described.
Abstract: L'hydroxymethyl-6 methyl-8a phenyl-7 perhydro pyrrolo [3,2-a] oxazolinone-4 est un reactif chiral permettant la synthese d'un derive de pyrrolo [1,8,8a-a] quinoleine precurseur d'alcaloides
TL;DR: This report represents the first total synthesis of the important natural metabolites of myo-inositol 1,3,4,5-tetrakisphosphate and (14) and significantly improved methods of preparation of (6) and (9).
Abstract: Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a–e), (7), (10), (12), and (16). These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14). This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).
TL;DR: In this article, total synthesis of the antitumor antibiotic pleurotin (1) and dihydropleurotin acid (2) was described. But the final stage of the synthesis involved the biomimetic conversion of dihydroproindan acid to pleuroin.
Abstract: Total syntheses of the antitumor antibiotic pleurotin (1) and dihydropleurotin acid (2) are described. Early stages of the synthesis feature the construction of a trans perhydroindan substructure using a stereoselective free-radical cyclization, and the final stage of the synthesis involves the biomimetic conversion of dihydropleurotin acid (2) to pleurotin (1)
TL;DR: The synthese totale de l'alcaloide du titre de structure benzopyranno-1 [5',6':6,7] indeno [1,2-b] indole a ete effectuee a partir de la perhydro benzo[e]indenone-1
Abstract: La synthese totale de l'alcaloide du titre de structure benzopyranno-1 [5',6':6,7] indeno [1,2-b] indole a ete effectuee a partir de la perhydro benzo[e]indenone-1
TL;DR: The general applicability of a four-component condensation for the formation of N-acyl-β-aryloxyprolines has been demonstrated in several model studies as mentioned in this paper.
Abstract: The general applicability of a four-component condensation for the formation of N-acyl-β-aryloxyprolines has been demonstrated in several model studies. The relative stereochemistry of the diastereoisomers obtained has been assigned from 1H n.m.r. studies, and confirmed by an X-ray analysis of one of the stereoisomers.
TL;DR: In this article, reaction de stannanes vinyliques avec des [alkyl-10 trifluoromesyloxy-2 tetrahydro-5,10,11,11a] pyrrolo [2,1-c] benzodiazepinedione (5,11)
Abstract: Reaction de stannanes vinyliques avec des [alkyl-10 trifluoromesyloxy-2 tetrahydro-5,10,11,11a] pyrrolo [2,1-c] benzodiazepinedione-5,11