12 research outputs found

    Strategic use of retro Diels-Alder reaction in the construction of β -carboxy-α-methylene-γ-lactones. Total synthesis of methylenolactocin and protolichesterinic acid

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    A facile route for the construction of β -carboxy-α-methylene-γ -lactone unit is described using retro Diels-Alder reaction as the key step. Using this protocol, total synthesis of (± )-methylenolactocin and (± )-protolichesterinic acid has been achieved

    Stereocontrolled total synthesis of (±)-β-necrodol

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    A total synthesis of racemic β -necrodol is described using an ortho-ester claisen rearrangement as the key step to dictate a high level of trans-1,3-diastereoselection on a cyclopentane derivative

    An unusual reaction course in Rh(I)-induced decarbonylation of γ,δ-unsaturated aldehyde. Total synthesis of (±)-iso-β-necrodol and (±)-β-necrodol

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    Decarbonylation of the γ,δ-unsaturated aldehydes (4 and 9), embodied in a sterically congested carbon network, with Wilkinson's catalyst followed a reaction course different from the normal decarbonylation or hydroacylation path. This investigation has led to the synthesis of iso-β-necrodol and the monoterpene β-necrodol

    Synthesis of methoxy and hydroxy containing tetralones: Versatile intermediates for the preparation of biologically relevant molecules

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    The synthesis of 5-hydroxy-6-methoxy-1-tetralone and the 7-hydroxy regioisomer along with the corresponding 5,7-dihyroxy analog has been achieved using an efficient directed metallation procedure followed by a regioselective methylene oxidation. This methodology represents a general synthetic route for the preparation of highly oxygenated tetralone analogs which are versatile building blocks for the construction of molecules of biological interest. © 2003 Elsevier Science Ltd. All rights reserved

    A new synthetic method for the reduction of imines by samarium-induced reaction<sup>†</sup>

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    1134-1139Samarium metal induced reduction of the imines towards the synthesis of secondary amines has been investigated

    Synthesis of a 2-aryl-3-aroyl indole salt (OXi8007) resembling combretastatin A-4 with application as a vascular disrupting agent

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    The natural products colchicine and combretastatin A-4 are potent inhibitors of tubulin assembly, and they have inspired the design and synthesis of a large number of small-molecule, potential anticancer agents. The indole-based molecular scaffold is prominent among these SAR modifications, leading to a rapidly increasing number of agents. The water-soluble phosphate prodrug 33 (OXi8007) of 2-aryl-3-aroylindole-based phenol 8 (OXi8006) was prepared by chemical synthesis and found to be strongly cytotoxic against selected human cancer cell lines (GI50 = 36 nM against DU-145 cells, for example). The free phenol, 8 (OXi8006), was a strong inhibitor (IC 50 = 1.1 μM) of tubulin assembly. The corresponding phosphate prodrug 33 (OXi8007) also demonstrated pronounced interference with tumor vasculature in a preliminary in vivo study utilizing a SCID mouse model bearing an orthotopic PC-3 (prostate) tumor as imaged by color Doppler ultrasound. The combination of these results provides evidence that the indole-based phosphate prodrug 33 (OXi8007) functions as a vascular disrupting agent that may prove useful for the treatment of cancer. © 2013 The American Chemical Society and American Society of Pharmacognosy

    2-(3-tert-butyldimethylsiloxy-4-methoxyphenyl)-6-methoxy-3-(3,4, 5-trimethoxybenzoyl)indole

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    In the crystal structure of the title compound, C32H39NO7Si, all geometric parameters fall within experimental error of expected values. The analysis of molecular-packing plots reveals an infinite two-dimensional linear array running parallel to the b axis, formed by one N-H⋯O intermolecular hydrogen-bonding interaction. Several potential C-H⋯O interactions are also present
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