High-yield direct synthesis of a new class of tertiary organolithium derivatives of polycyclic hydrocarbons

1983 ◽  
Vol 48 (18) ◽  
pp. 2975-2981 ◽  
Author(s):  
G. Molle ◽  
P. Bauer ◽  
J. E. Dubois
Keyword(s):  
Direct Synthesis ◽  
High Yield ◽  
Polycyclic Hydrocarbons ◽  
New Class ◽  
Derivatives Of

Direct synthesis of organic derivatives of silicon using nonhalogenated organic compounds

1970 ◽  
Vol 9 (5) ◽  
pp. 1071-1075 ◽  
Author(s):  
William E. Newton ◽  
Eugene G. Rochow
Keyword(s):  
Organic Compounds ◽  
Direct Synthesis ◽  
Derivatives Of

Bis(ether) derivatives of tetrakis(2-hydroxyphenyl)ethene — Direct synthesis of (E)- and (Z)-bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene via the McMurry olefination reaction

2006 ◽  
Vol 84 (10) ◽  
pp. 1250-1253 ◽  
Author(s):  
Mee-Kyung Chung ◽  
Paul Fancy ◽  
Jeffrey M Stryker
Keyword(s):  
Supramolecular Chemistry ◽  
Direct Synthesis ◽  
Protecting Groups ◽  
Tert Butyl ◽  
Orthogonal Protection ◽  
Protection Strategies ◽  
Titanium Trichloride ◽  
Sterically Hindered ◽  
Derivatives Of

The direct synthesis of sterically hindered, partially etherified derivatives of tetrakis(2-hydroxyphenyl)ethene is reported by using the McMurry reductive olefination reaction on a range of differentially substituted 2,2′-dialkoxy benzophenone substrates. Three orthogonal protection strategies are demonstrated, incorporating β-silylethyl, 3-butenyl, and tert-butyl protecting groups, respectively, into the starting benzophenones. The latter proved most efficient, with both the McMurry coupling and deprotection steps occurring concomitantly under the McMurry conditions to directly yield the desired bis(2-hydroxyphenyl)-bis(2-methoxyphenyl)ethene as a 1:1 mixture of E- and Z-diastereoisomers.Key words: preorganized polyaryloxide ligands, McMurry olefination, titanium trichloride, supramolecular chemistry, tetrakis(2-hydroxyphenyl)ethene, 2,2′-disubstituted benzophenone.

scholarly journals Epoxy derivatives of aromatic polycyclic hydrocarbons. The preparation of benz[a]anthracene 8,9-oxide and 10,11-dihydrobenz[a]anthracene 8,9-oxide and their metabolism by rat liver preparations

1971 ◽  
Vol 125 (1) ◽  
pp. 159-168 ◽  
Author(s):  
P. Sims
Keyword(s):  
Rat Liver ◽  
Reduced Glutathione ◽  
Mercapturic Acids ◽  
Polycyclic Hydrocarbons ◽  
Glutathione Conjugates ◽  
Liver Homogenates ◽  
Derivatives Of ◽  
Related Compounds

The syntheses of 10,11-dihydrobenz[a]anthracene 8,9-oxide, benz[a]anthracene 8,9-oxide and 9-hydroxybenz[a]anthracene are described, together with those of a number of related compounds. The epoxides react both chemically and enzymically with water to yield the corresponding dihydrodiols and with reduced glutathione to form glutathione conjugates, and they react chemically with N-acetylcysteine to yield the corresponding mercapturic acids. 8,9-Dihydro-8,9-dihydroxybenz[a]anthracene, formed enzymically from benz[a]anthracene 8,9-oxide, was identical with a dihydrodiol formed when benz[a]anthracene was metabolized by rat liver homogenates. Similarly 10,11-dihydrobenz[a]anthracene 8,9-oxide yielded a dihydrodiol identical with the product formed when 10,11-dihydrobenz[a]anthracene was metabolized.

scholarly journals General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties

2021 ◽  
Author(s):  
Jessica E. Pigga ◽  
Julia Rosenberger ◽  
Andrew Jemas ◽  
Samantha Boyd ◽  
Olga Dmitrenko ◽  
...  
Keyword(s):  
Physicochemical Properties ◽  
Large Scale ◽  
High Reactivity ◽  
Diels Alder ◽  
Synthetic Methods ◽  
High Yield ◽  
Physiochemical Properties ◽  
New Class ◽  
State Models

<p><i>trans</i>-Cyclooctenes (TCOs) are essential partners for the fastest known bioorthogonal reactions, but current synthetic methods are limited by poor diastereoselectivity. Especially hard to access are hydrophilic TCOs with favorable physicochemical properties for live cell or <i>in vivo </i>experiments. Described is a new class of TCOs, ‘a-TCOs’, that is prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a <i>trans</i>-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.</p>

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