87184-81-4Relevant articles and documents
Total syntheses of multiple cladiellin natural products by use of a completely general strategy
Clark, J. Stephen,Berger, Raphaelle,Hayes, Stewart T.,Senn, Hans Martin,Farrugia, Louis J.,Thomas, Lynne H.,Morrison, Angus J.,Gobbi, Luca
, p. 673 - 696 (2013)
The enantioselective total syntheses of 10 cladiellin natural products have been completed, starting from the known allylic alcohol (+)-14, which can be prepared in large quantities. The bridged tricyclic core of the cladiellins has been constructed via three ring-forming reactions: (i) an intramolecular reductive cyclization between an aldehyde and an unsaturated ester, mediated by samarium(II) iodide, to form a tetrahydropyranol; (ii) reaction of a metal carbenoid, generated from a diazo ketone, with an ether to produce an ylide-like intermediate that rearranges to produce E- or Z-oxabicyclo[6.2.1]-5-undecen-9- one; and (iii) a Diels-Alder cycloaddition reaction to construct the third ring found in the core structure of the cladiellins. The key ring-forming reaction, in which a diazo ketone is converted into a bridged bicyclic ether, can be tuned to give either of the isomeric oxabicyclo[6.2.1]-5-undecen-9-ones as the major product by switching from a copper to a rhodium catalyst and selecting the appropriate reaction conditions. The tricyclic products obtained from the three-step sequence involving the Diels-Alder cycloaddition reaction can be employed as advanced intermediates to prepare a wide range of cladiellin natural products.
Enantio and Stereoselective Synthesis of (5R,6S)-6-Acetoxy-hexadecanolide, a Mosquito Oviposition Attractant Pheromone
Bonini, Carlo,Checconi, Massimo,Righi, Giuliana,Rossi, Leucio
, p. 4111 - 4116 (1995)
The enantio and stereoselective synthesis of (5R,6S)-6-acetoxy-hexadecanolide is described via chemo, regio and stereoselective opening with LiI of a chiral epoxy alcohol precursor.
Intramolecular 4 + 3 cycloadditions. Theoretical and experimental evaluation of endo/exo preferences of a cyclopentenyl cation
Cramer,Harmata,Rashatasakhon
, p. 5641 - 5644 (2001)
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Unexpected dehydrogenation products in the furan series arising from ruthenium-catalyzed 4-oxo-1,6-enyne metathesis
Evanno, Laurent,Nay, Bastien,Bodo, Bernard
, p. 1559 - 1565 (2005)
Metathesis of 4-oxo-1,6-enynes afforded the usual dihydrofuran products accompanied for the first time by unexpected side products identified as the corresponding furans. It probably arose from ruthenium-catalyzed dehydrogenation of dihydrofurans in the m
Building addressable libraries: The use of "safety-Catch" linkers on microelectrode arrays
Bi, Bo,Maurer, Karl,Moeller, Kevin D.
, p. 17405 - 17407 (2010)
A "safety-catch" linker strategy has been used to site-selectively cleave and characterize molecules from a microelectrode array. The linkers are attached to the array by means of an ester and contain either a protected amine or protected alcohol nucleophile that can be released using acid generated at the microelectrodes.
Micellar Catalysis for Sustainable Hydroformylation
Calamante, Massimo,Dei, Filippo,Maramai, Samuele,Migliorini, Francesca,Petricci, Elena
, p. 2794 - 2806 (2021/05/03)
It is here reported a fully sustainable and generally applicable protocol for the regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation in tandem with intramolecular hemiacetalization thus demonstrating the compatibility with a broad variety of functional groups. The reaction is efficient even in large scale and the catalyst and micellar water phase can be reused at least 5 times without any impact in reaction yields. The efficiency and sustainability of this protocol is strictly related to the in situ transformation of the aldehyde into the corresponding Bertagnini's salt that precipitates in the reaction mixture avoiding organic solvent mediated purification steps to obtain the final aldehydes as pure compounds.
SCALEABLE PREPARATION OF POLYKETIDES
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Paragraph 0253-0256; 0412-0415, (2021/02/12)
Disclosed herein, inter alia, are methods of making polyketide compounds.
Chiral geminal disilyl alkane compound, synthesis method and applications thereof
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Paragraph 0204; 0205; 0206; 0207; 0210, (2019/01/14)
The present invention discloses a chiral geminal disilyl alkane compound, which is represented by a formula V, wherein * represents a chiral carbon atom in the formula V. The invention discloses a synthesis method of the chiral geminal disilyl alkane compound, wherein the synthesis method comprises: carrying out a reaction in the presence of a reducing agent by using alkyne represented by a formula I, dihydrosilane represented by a formula II and trihydrosilane represented by a formula III as raw materials and using Xantphos-CoBr2 and a chiral CoX2-OIP complex as catalysts under an inert gas to prepare the chiral geminal disilyl alkane compound represented by the formula V. According to the present invention, the method has characteristics of mild reaction condition, simple operation, highatomic economy, no requirement of the addition of any other toxic transition metals (such as ruthenium, rhodium, palladium and the like) salts, high yield and high enantioselectivity, and has great practical value in the synthesis of drugs and materials, wherein the yield is generally 50-85%, and the enantioselectivity is generally 93-99%. The formulas I, II, III and V are defined in the specification.
