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Showing papers in "Tetrahedron Letters in 1987"


Journal ArticleDOI
Hans Rink1
TL;DR: In this article, a trialkoxy-diphenyl-methylester and amide linkage for solid-phase peptide synthesis with Fmoc strategy is described, which can be smoothly cleaved with weak acid, resulting in fragments with intact side-chain protection.

859 citations


Journal ArticleDOI
TL;DR: In this article, the use of lithium hydroperoxide for the highly regioselective hydrolysis of a range of carboximides is described, and several cases are provided where the reagent exhibited dramatically different than the complementary reactions with hydroxide.

412 citations


Journal ArticleDOI
TL;DR: Sodium borohydride reduction of β-hydroxyketones in presence of alkoxydialkylboranes 1−7 as complexing agents, produced 1,3- syn diols in at least 98:2 ratio as discussed by the authors.

366 citations


Journal ArticleDOI
TL;DR: In this article, a novel polyether toxin, yessotoxin, was isolated from scallops implicated in diarrhetic shellfish poisoning, and its planar structure was proposed by means of modern NMR techniques.

343 citations


Journal ArticleDOI
TL;DR: In this article, thermally stable 1,2-dioxetanes bearing tert-butyldimethylsilyloxyaryl groups have been prepared and react with fluoride ion at ambient temperature in MeCN and DMSO with efficiencies up to 25%.

235 citations


Journal ArticleDOI
TL;DR: In this paper, the authors propose a rapid and efficient way to obtain esters of primary and secondary alcohols, provided there is a hydrogen atom on the carbon adjacent to the carbonyl of the acyl moiety.

210 citations


Journal ArticleDOI
TL;DR: Structure 1 is proposed to represent the product of reaction of methyl thioglycolate with the neocarzinostatin chromophore and a mechanism for the formation of 1 is presented which provides a rationale for the nucleophilic activation of neocarcinostatin.

210 citations


Journal ArticleDOI
TL;DR: The preparation of an aryl phosphate-substituted 1,2-dioxetane and the enzymatic cleavage of this chemiluminescent dioxetanes in aqueous buffer with alkaline phosphatase are described.

209 citations


Journal ArticleDOI
TL;DR: In this paper, a phenyldimethylsilyl group attached to carbon can be converted into a hydroxyl group using either bromine or mercuric ion in an acetic acid solution of peracetic acid.

176 citations


Journal ArticleDOI
TL;DR: A thermally stable 1,2-dioxetane bearing a naphthyl acetate group is enzymatically cleaved in aqueous buffer to generate chemiluminescence at ambient temperature.

174 citations


Journal ArticleDOI
TL;DR: In the presence of n -Bu4NCl, DMF and an appropriate base (Na2CO3, NaOAc or Et3N) cyclize nitrogen-containing o -iodoaryl alkenes to indoles, indolines,3 oxindoles, quinolines and isoquinolines.

Journal ArticleDOI
TL;DR: In this article, secondary amines with hydrogen peroxide in the presence of selenium dioxide catalyst at room temperature gives nitrones, which are versatile synthetic intermediates, highly efficiently.

Journal ArticleDOI
Peter Sieber1
TL;DR: The synthesis of the new polymeric support of type 7 for the preparation of C-terminal peptide amides by the Fmoc method is described and Cleavage of the peptideAmides is performed by very mild acidolysis.

Journal ArticleDOI
TL;DR: The lower order mixed cuprate derived from CuCN and 2-lithiothiophene (i.e., 2-ThCu(CN)Li) is found to have excellent shelf life, thereby providing an easily formed yet itself unreactive precursor to higher order mixed organocuprates as discussed by the authors.

Journal ArticleDOI
TL;DR: A convenient method for the preparation of 65–85 g quantities of Cp2Zr(H)Cl, Schwartz's reagent has been developed and is of high purity and has several advantages over the reagent prepared by previously reported methods.

Journal ArticleDOI
TL;DR: The cytotoxic extract of Psammaplysilla sp. collected from Tonga contains monobromo tyrosine derivatives, 3-bromo-4-hydroxyphenylacetonitrile (1), which is known and psammaplin A (2) which is the first disulfide to be isolated from a sponge.

Journal ArticleDOI
TL;DR: Using [Cp(Me)5Rh(bipy)C1]C1 (1) as redox catalyst for the continous NADH regeneration, it was possible to perform an electrochemically driven enzymatic reduction of pyruvate to D-lactate catalyzed by D-LDH at a rate of 5 turnovers per hour as discussed by the authors.

Journal ArticleDOI
Peter Sieber1
TL;DR: In this paper, Fmoc-amino acids are added to 4-alkoxybenzyl alcohol polystyrene by 2,6-dichlorobenzoyl chloride, which is free of the two side-reactions observed with dicyclohexyl carbodiimide/4-dimethylaminopyridine, viz. racemization and dipeptide formation.

Journal ArticleDOI
TL;DR: In this paper, Lycopadiene (2.6R,10R,14,19,23R,27R,31 -octamethyldotriaconta- 14(E), 18(E)-diene) has been isolated from the hexane extract of new strains of the green colonial alga Botryococcus braunii.

Journal ArticleDOI
TL;DR: In this paper, the stereoselective aldol addition reactions of chiral haloacetate enolates is reported. And the conversion of these adducts to enantiomerically pure anti-β-hydroxy-α-amino acids is demonstrated.

Journal ArticleDOI
TL;DR: Keramamine-A and -B, two β-carboline alkaloids with a 13 membered ring have been isolated from the Okinawan marine sponge Pellina sp. as mentioned in this paper.

Journal ArticleDOI
TL;DR: The title compounds were isolated from a marine sponge collected off Okinawa and determined by X-ray and shown to be 1-β-carbolines as mentioned in this paper, the 2-ethyl-N-azacycloundec-6-ene derivative of dihydromanzamine A.

Journal ArticleDOI
TL;DR: Aryl boronic acids have been obtained by metalation-B(OMe) 3 or metalation silylation-ipso borodesilylation sequences as discussed by the authors.

Journal ArticleDOI
TL;DR: The chiral N-acyl oxazolidones 2, as the derived dibutyl boron enolates, have been demonstrated to undergo diastereoselective bromination and subsequent azide displacement to give the α-azido carboximides 4a (5 cases) as mentioned in this paper.

Journal ArticleDOI
TL;DR: An optically active ferrocenylphosphine ligand containing 2-(morpholino)ethylamino or 2-(piperidino)ethylamino group on the ferrocene side chain was effective for the gold-catalyzed aldol reaction of methyl isocyanoacetate with aldehydes as discussed by the authors.

Journal ArticleDOI
TL;DR: In this article, the synthesis of ( + )-pinitol in 35% overall yield from benzene has been achieved where the key step involved microbial oxidation of benzene to cis -1,2-dihydroxycyclohexa-3,5-diene.

Journal ArticleDOI
TL;DR: In this paper, secondary amines react with carbon dioxide and terminal alkynes in the presence of a catalytic amount of 4-1,5-cyclooctadiene (COD), 6- 1,3,5 cyclooctatriene [Ru(COD)(COT)] and tertiary phosphine in toluene to give enol carbamates in good yields with high regio and stereoselectivity.

Journal ArticleDOI
TL;DR: In this article, Ntert-Butoxycarbonylated 2-oxazolidinones and tetrahydro-2oxazinones are smoothly cleaved to acyclic N-Boc-amino alcohols on treatment with catalytic amounts of cesium carbonate at room temperature.

Journal ArticleDOI
TL;DR: In this paper, it was shown that RCu add readily in a conjugate fashion to enones in the presence of TMSCl and TMEDA to give high yields of trimethylsilyl enol ethers.

Journal ArticleDOI
TL;DR: In this article, the reductive homocoupling of aromatic and α, β-unsaturated aldehydes was found to yield symmetrical 1, 2-diols with high threo -selectivity.