A new synthesis of chasmanine and 13-desoxydelphonine: a preferred route to the aromatic intermediate

Thomas Y. R. Tsai; Krishnan P. Nambiar; Dikran Krikorian; Maurizio Botta; Rinaldo Marini-Bettolo; Karel Wiesner

doi:10.1139/v79-341

A new synthesis of chasmanine and 13-desoxydelphonine: a preferred route to the aromatic intermediate

Canadian Journal of Chemistry ◽

10.1139/v79-341 ◽

1979 ◽

Vol 57 (16) ◽

pp. 2124-2134 ◽

Cited By ~ 11

Author(s):

Thomas Y. R. Tsai ◽

Krishnan P. Nambiar ◽

Dikran Krikorian ◽

Maurizio Botta ◽

Rinaldo Marini-Bettolo ◽

...

Keyword(s):

Efficient Synthesis ◽

Compound I ◽

New Synthesis

An efficient synthesis (stereo- and regiospecific) of compound I (Scheme I) from o-cresol is described.

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A New Synthesis of 6-Hydroxydopamine

Canadian Journal of Chemistry ◽

10.1139/v72-488 ◽

1972 ◽

Vol 50 (18) ◽

pp. 3075-3079 ◽

Cited By ~ 2

Author(s):

Pius A. Wehrli ◽

F. Pigott ◽

V. Chu

Keyword(s):

Efficient Synthesis ◽

New Synthesis ◽

6 Hydroxydopamine

An efficient synthesis of 6-hydroxydopamine is described. The key step involves oxidation of an N-protected 3-hydroxy-4-methoxyphenethylamine to the corresponding p-quinone by means of Fremy's salt.

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On cardioactive steroids. IV. A new synthesis of cardenolides

Canadian Journal of Chemistry ◽

10.1139/v81-206 ◽

1981 ◽

Vol 59 (9) ◽

pp. 1403-1404 ◽

Cited By ~ 11

Author(s):

Rinaldo Marini-Bettolo ◽

Petr Flecker ◽

Thomas Y. R. Tsai ◽

Karel Wiesner

Keyword(s):

Efficient Synthesis ◽

New Synthesis ◽

Cardioactive Steroids

A new and efficient synthesis of Digitalis cardenolides via methoxyfuryl intermediates is described.

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Rapid and Efficient Synthesis of Hydroxytriarylmethanes under Ultra Sonic Irradiation Using Keggin Heteropolyacids and Preyssler Catalysts in Green Conditions

Organic Chemistry International ◽

10.1155/2013/502343 ◽

2013 ◽

Vol 2013 ◽

pp. 1-5 ◽

Cited By ~ 2

Author(s):

Hooshang Hamidian

Keyword(s):

Ultrasonic Irradiation ◽

Catalytic Amount ◽

Efficient Synthesis ◽

Efficient Catalyst ◽

New Synthesis ◽

Keggin Heteropolyacids ◽

Green Conditions

A new synthesis of hydroxytriarylmethane derived from the reaction of 2-sulfobenzoic anhydride and phenols in the presence of heteropolyacids as green, reusable, and efficient catalyst (using catalytic amount) under ultrasonic irradiation is reported in this paper.

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Activation of cytochrome c to a peroxidase compound I-type intermediate by H2O2: relevance to redox signalling in apoptosis

Biochemical Society Symposium ◽

10.1042/bss0710097 ◽

2004 ◽

Vol 71 ◽

pp. 97-106 ◽

Cited By ~ 10

Author(s):

Mark Burkitt ◽

Clare Jones ◽

Andrew Lawrence ◽

Peter Wardman

Keyword(s):

Cytochrome C ◽

Hydroxyl Radical ◽

Redox Regulation ◽

Chemotherapeutic Agents ◽

Tyrosyl Radical ◽

Compound I ◽

Definitive Evidence ◽

Enhanced Production ◽

Physico Chemical

The release of cytochrome c from mitochondria during apoptosis results in the enhanced production of superoxide radicals, which are converted to H2O2 by Mn-superoxide dismutase. We have been concerned with the role of cytochrome c/H2O2 in the induction of oxidative stress during apoptosis. Our initial studies showed that cytochrome c is a potent catalyst of 2′,7′-dichlorofluorescin oxidation, thereby explaining the increased rate of production of the fluorophore 2′,7′-dichlorofluorescein in apoptotic cells. Although it has been speculated that the oxidizing species may be a ferryl-haem intermediate, no definitive evidence for the formation of such a species has been reported. Alternatively, it is possible that the hydroxyl radical may be generated, as seen in the reaction of certain iron chelates with H2O2. By examining the effects of radical scavengers on 2′,7′-dichlorofluorescin oxidation by cytochrome c/H2O2, together with complementary EPR studies, we have demonstrated that the hydroxyl radical is not generated. Our findings point, instead, to the formation of a peroxidase compound I species, with one oxidizing equivalent present as an oxo-ferryl haem intermediate and the other as the tyrosyl radical identified by Barr and colleagues [Barr, Gunther, Deterding, Tomer and Mason (1996) J. Biol. Chem. 271, 15498-15503]. Studies with spin traps indicated that the oxo-ferryl haem is the active oxidant. These findings provide a physico-chemical basis for the redox changes that occur during apoptosis. Excessive changes (possibly catalysed by cytochrome c) may have implications for the redox regulation of cell death, including the sensitivity of tumour cells to chemotherapeutic agents.

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