- Total Stereospecific Synthesis of (3E,7Z)-Tetradecadienyl Acetate, the Major Sex Pheromone Component of the Potato Pest Symmetrischema tangolias
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(3E,7Z)-Tetradecadienyl acetate, the major sex pheromone component of the potato pest Symmetrischema tangolias (Gyen), was stereoselectively synthesized from the commercially available 3-bromo-1-propanol via the stereospecific reduction of alkyne with lit
- Awalekar, Ramchandra,Mohire, Priyanka,Patravale, Ajinkya,Salunkhe, Shilpa,Usmani, Shams,Jamale, Dattatray,Hangirgekar, Shankar,Kolekar, Govind,Anbhule, Prashant
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p. 1000 - 1004
(2021/11/18)
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- Oxidative Prins and Prins/Friedel-Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C-H activation
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1-Benzyl ethers of (E)- and (Z)-hex-3-en-1,6-diols and hept-3-en-1,7-diols undergo a smooth oxidative cyclization with DDQ in the presence of In(OTf) 3 through a sequential C-H bond activation and an intramolecular Prins cyclization to afford t
- Subba Reddy,Borkar, Prashant,Yadav,Purushotham Reddy,Kunwar,Sridhar,Gree, Rene
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supporting information; experimental part
p. 1349 - 1358
(2012/03/27)
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- Branched-chain and unsaturated 1,7-diaminoheptane derivatives as deoxyhypusine synthase inhibitors
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Deoxyhypusine synthase catalyzes the first step in the posttranslational biosynthesis of the unusual amino acid hypusine [Nε-(4-amino-2- hydroxybutyl)lysine] in eukaryotic translation initiation factor 5A (eIF- 5A). elF-5A and its single hypusine residue are essential for cell proliferation. Two series of 1,7-diaminoheptane derivatives were prepared and tested as inhibitors of human deoxyhypusine synthase. These include branched- chain saturated derivatives and both branched- and straight-chain unsaturated derivatives providing size and positional variation in branching and different torsional constraints. Of the branched-chain compounds, 7-amino-1- guanidinooctane (39) proved to be the most potent inhibitor in vitro (IC50, 34 nM), while 1,7-diamino-trans-hept-3-ene (20a) displayed the greatest inhibition (IC50, 0.7 μM) among the unsaturated compounds. Compound 39 also provided effective inhibition of hypusine production in Chinese hamster ovary cells in culture. Considerations of the in vitro inhibition data reported here, along with earlier findings, allowed some speculation concerning the conformation of the substrate spermidine during its productive interaction at the active site of deoxyhypusine synthase.
- Lee, Young Bok,Folk
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p. 253 - 270
(2007/10/03)
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- Formation of 14-membered carbocycles by intramolecular Michael addition on ynones and enones
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The base-catalyzed intramolecular Michael addition of substituted malonates on ynones or enones proceeds efficiently to give the 14-membered carbocycles.
- Girard, Suzanne,Deslongchamps, Pierre
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p. 1265 - 1273
(2007/10/02)
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- Cyclopenteneheptenoic acid derivatives and method of preparation thereof
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This invention relates to a novel cyclopenteneheptenoic acid derivative having the following formula STR1 wherein R1 is hydrogen, --COCH3, --COCF3, --CO--phenyl, or a hydroxyl protecting group such as tetrahydropyranyl, tetrahydrofuranyl, or tri-lower alkylsilyl; wherein R2 is --CH2 OR1, --COOH, --COOR, --CHO, --CH2 --OSi(R12)3, STR2 wherein R is lower alkyl and each R12 is independently lower alkyl or aryl; and wherein Y is ethylene, cis-vinylene, trans-vinylene, or acetylene. Also disclosed is a novel process for preparation of the above-defined cyclopenteneheptenoic acid derivative. This process involves coupling of a higher order cuprate complex with a chiral cyclopentene compound. The resultant product is particularly useful as a starting compound for high yield synthesis of optically active prostaglandins.
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