Showing papers on "Total synthesis published in 1984"
TL;DR: Recent advances and examples of the intramolecular Diels-Alder reaction are summarized and applications to the total synthesis of natural products, both completed and in progress, noted as discussed by the authors.
Abstract: Recent advances and examples of the intramolecular Diels–Alder reaction are summarized and applications to the total synthesis of natural products, both completed and in progress, noted. A detailed...
296 citations
TL;DR: In this article, the authors proposed a method for the reduction of prochiral ketones and the elaboration of a procedure for double vicinal CC-coupling with enones to enable a one-pot synthesis of the complete prostaglandin skeleton by linking a chiral 4-oxygenated 2-cyclopentenone unit and two side-chain blocks.
Abstract: The role played by prostaglandins (PGs) in the human body is bewitching. Following the elucidation of their structures in the early 1960s, tremendous efforts were made for the realization of an efficient chemical synthesis, since a sufficient supply of such very rare, naturally occurring local hormones relies solely on their total synthesis. Of the many synthetic routes described in the literature, the majority of which are linear or sequential in nature, the Corey synthesis is perhaps the most versatile; so far more than 5000 prostaglandin analogues have been prepared and have been tested biologically. Some natural prostaglandins and their analogues are already in clinical use. In view of the continuing expansion of this field, we have been fascinated with the concept of developing a highly convergent entry to prostaglandins based on a new strategy. The discovery of a highly enantioselective method for the reduction of prochiral ketones and the elaboration of a procedure for double vicinal CC-coupling with enones have enabled a one-pot synthesis of the complete prostaglandin skeleton by linking a chiral 4-oxygenated 2-cyclopentenone unit and two side-chain blocks. This approach is efficient and flexible and allows the direct production of all the naturally occuring prostaglandins and a wide spectrum of analogues.
208 citations
114 citations
TL;DR: A total synthesis of 2,2′-N; 3,3′-Otetraquis[(R)-3-hydroxytetradecanoyl]-β(1-6)-D-glucosamine disaccharide 1,4′-diphosphate is described in this paper.
110 citations
103 citations
TL;DR: The extent of diastereoselectivity associated with the reactions of nitrile oxides with alkenes bearing an allylic oxygen substituent has been studied and a synthesis of (±)-blastmycinone is reported which combines the two foregoing aspects of stereocontrol.
Abstract: The extent of diastereoselectivity associated with the reactions of nitrile oxides with alkenes bearing an allylic oxygen substituent has been studied. Reasonable levels of such diastereoselectivity have been found when the tert-butyldimethylsilyl ether derivative of 3-buten-2-ol (5) or (+)-(S)-isopropylidene-3-butene-1,2-diol (1) are employed as dipolarophiles. The stereochemical course of these cycloaddition reactions has been proven rigorously through the transformation of the adducts to known γ-lactones. The stereochemistry associated with the metalation/alkylation of 5-alkoxymethyl-substituted isoxazolines has also been probed in order to further expand the use of these heterocycles as aldol equivalents in natural products total synthesis. A synthesis of (±)-blastmycinone (34) is reported which combines the two foregoing aspects of stereocontrol. The levels of regio- and stereoselectivity found in the cycloaddition reactions of the cis- and trans-disubstituted alkenes 35 and 39 prepared from isopropylidene-D-glyceraldehyde are also discussed. A single example of the reaction of a chiral alkene with a chiral nitrile oxide is presented.
97 citations
97 citations
91 citations
TL;DR: A virtually complete asymmetric control in the synthesis of 2,3-disubstituted butan-4-olide (10) was demonstrated by employing the butenolide as the chiral acceptor for the conjugate 1,4-addition as discussed by the authors.
89 citations
86 citations
TL;DR: In this paper, the cyclisation of methoxy-7 cycloheptadiene-2,4 propanal intermediaire has been studied in the context of drug design.
Abstract: Synthese des composes du titre a partir de la cycloheptatrienone L'etape cle est la cyclisation du methoxy-7 cycloheptadiene-2,4 propanal intermediaire
TL;DR: The absolute configuration of castanospermine has been determined by total synthesis to be as shown in this paper, where the absolute configuration is shown to be the same as that of castanetspermine.
TL;DR: In this paper, a practical approach to the synthesis of acivicin and bromo-acivicin has been developed, based on a thermal [3,3] sigmatropic rearrangement of trichloroimidate.
TL;DR: In this article, a total synthesis of 1α,25S,26-trihydroxycholecalciferol (2) has been accomplished via an efficient convergent approach via a regiospecific and diastereoselective 1,3-dipolar cycloaddition with methyl methacrylate.
TL;DR: Synthese du compose du titre a partir du trimethyleneacetal du decahydro dimethyl-13,15 dioxo-2,10 ethyl-16 oxacyclohexadecinnecarbothialdehyde-6.
Abstract: Synthese du compose du titre a partir du trimethyleneacetal du decahydro dimethyl-13,15 dioxo-2,10 ethyl-16 oxacyclohexadecinnecarbothialdehyde-6. Stereoselectivite, controle cinetique
TL;DR: A 16-membered macrolide antibiotic, protomycinolide IV, was synthesized from two fragments to which the chirality was introduced by asymmetric epoxidation of the appropriately chosen allylic alcohols.
TL;DR: On prepare le titre a partir de la cetone de Wieland-Miescher par une synthese in 9 etapes avec un rendement de 13% as discussed by the authors.
Abstract: On prepare le compose du titre a partir de la cetone de Wieland-Miescher par une synthese en 9 etapes avec un rendement de 13%
TL;DR: The total synthesis of the methyl ester of the antibiotic lavendamycin (4a) by an 8-step sequence from 8-methoxyquinaldic acid (6) is described in this article.
TL;DR: On prepare la clavulone I et son isomere 5,6-(E), analogues des prostaglandines, a partir du cyclopentadienure de lithium et du iodo-1 octyne-2 as discussed by the authors.
Abstract: On prepare la clavulone I et son isomere 5,6-(E), analogues des prostaglandines, a partir du cyclopentadienure de lithium et du iodo-1 octyne-2
TL;DR: On prepare les composes du titre a partir de l'acide cyclohexene-3 carboxylique via une todolactone as mentioned in this paper.
Abstract: On prepare les composes du titre a partir de l'acide cyclohexene-3 carboxylique via une todolactone