scholarly journals Isolation and Absolute Stereochemistry of Optically Active Sydonic Acid fromGloniumsp. (Hysteriales, Ascomycota)

2009 ◽  
Vol 73 (1) ◽  
pp. 203-204 ◽  
Author(s):  
Shinji KUDO ◽  
Takanori MURAKAMI ◽  
Junsuke MIYANISHI ◽  
Kazuaki TANAKA ◽  
Noboru TAKADA ◽  
...  
Keyword(s):  
Optically Active ◽  
Absolute Stereochemistry

Antioestrogenic and antifertility compounds. III. Enantiomers of (±)-hexoestrol and its homologues

1970 ◽  
Vol 23 (8) ◽  
pp. 1605 ◽  
Author(s):  
DJ Collins ◽  
JJ Hobbs
Keyword(s):  
Butyric Acid ◽  
Active Site ◽  
Oestrogen Receptor ◽  
Optically Active ◽  
Valeric Acid ◽  
Absolute Stereochemistry

(�)-2,3-Bis(p-hydroxyphenyl)butane (5a) and (&)-3,4-bis(p-hydroxyphenyl)-hexane (5c) were resolved, and absolute stereochemistry of the former was established as (-)-(2R,3R) by correlation with (+)-(R)-2,3-bis(p-methoxyphenyl)but-1-en. The (+) and (-) isomers of erythro-2,3-bis(p-hydroxyphenyl)pentane (Sb) were synthesized from (-)- and (+)-erythro-2,3-bis(p-methoxyphenyl)valeric acid, respectively. (+)-erythro-2,3-Bis(p-hydroxyphenyl)pentane (5b) was shown to have the (2R,3S) configuration, and (+)-threo-(b) the (2S,3S) configuration, by correlation with (-)-(8)-2,3-bis(p-methoxyphenyl)pent-1-ene. It follows that the configuration of erythro-2,3-bis(p-methoxyphenyl)-valeric and the corresponding-butyric acid is (+)-(2S,3R). Interaction of optically active hexoestrol and its homologues with the oestrogen receptor active site is discussed in terms of steroid stereochemistry.

Stereospecific synthesis of hexahydrobenzopyrroloisoquinoline and tetrahydrobenzisoquinoline derivatives

1984 ◽  
Vol 37 (4) ◽  
pp. 819 ◽  
Author(s):  
E Gellert ◽  
N Kumar
Keyword(s):  
Amino Acids ◽  
Metal Hydride ◽  
Optically Active ◽  
Stereospecific Synthesis ◽  
Hydride Reduction ◽  
The Absolute ◽  
Absolute Stereochemistry

New optically active hexahydrobenzopyrroloisoquinoline and tetrahydrobenzisoquinoline derivatives have been synthesized. Metal hydride reduction of the cyclic amino ketones, prepared by mild Friedel-Crafts type intramolecular acylation of N-naphthalenylmethyl amino acids, yielded pairs of diastereoisomeric alcohols. The absolute stereochemistry and some features of the n.m.r. spectra of hexahydrobenzopyrroloisoquinolines, tetrahydrobenzisoquinoline and those of their intermediates are discussed.

Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines

2008 ◽  
Vol 85 (5) ◽  
pp. 698 ◽  
Author(s):  
Damian A. Allen ◽  
Anthony E. Tomaso ◽  
Owen P. Priest ◽  
David F. Hindson ◽  
Jamie L. Hurlburt
Keyword(s):  
Optically Active ◽  
The Absolute ◽  
Absolute Stereochemistry

Terpenoid chemistry. XXI. ( - )-Epingaione, ( - )-Dehydrongaione, ( - )-Dehydroepingaione, and ( - )-Deisopropylngaione, toxic furanoid sesquiterpenoid ketones from Myoporum deserti

1973 ◽  
Vol 26 (2) ◽  
pp. 375 ◽  
Author(s):  
WD Hamilton ◽  
RJ Park ◽  
GJ Perry ◽  
MD Sutherland
Keyword(s):  
Essential Oils ◽  
Optically Active ◽  
Aqueous Alkali ◽  
Liver Pathology ◽  
Liver Lesions ◽  
Literature Report ◽  
The Absolute ◽  
Absolute Stereochemistry

The isolation and properties of four furanoid sesquiterpene ketones from various specimens of the stock-poisoning shrub Myoporum deserti are described. (-)-Epingaione [(-)-(1S,4S)-β-(4,8-dimethyl-6-oxo-1,4- epoxynonyl)furan] may be epimerized to (-)-ngaione either thermally or by base. (-)-Dehydrongaione [(-)-(1S,4R)-β-(4,8-dimethyl-6-oxo-1,4- epoxynon-7-enyl)-furan] is hydrogenated to (-)-ngaione and is equilibrated either thermally or by base with the unconjugated isopropenylic non-8-enyl isomer and (-)-dehydroepingaione [the (1S,4S)- diastereomer], which is hydrogenated to (-)-epingaione. Treatment of dehydrongaione and its epimer with aqueous alkali yields (-)- deisopropylngaione and its epimer by a retroaldol reaction. ��� The argument used by Matsuura1 to deduce the absolute stereochemistry of (+)-ngaione (ipomeamorone) is invalid since, contrary to the literature report, the ipomic lactone obtained from the oxidation of ngaione is not optically active. ��� Specimens of M. deserti have been found which yield essential oils containing each of the four furanoid ketones (-)-ngaione, (-)- epingaione, (-)-dehydrongaione, and (-)-dehydroepingaione free or virtually free from the others. The presence of a few percent of (-)- deisopropylngaione in one (dehydrongaione-rich) M. deserti oil has been demonstrated. ��� (+)-Ngaione, (-)-epingaione, and a mixture of (-)-dehydrongaione and (-)-dehydroepingaione all cause the typical (-)-ngaione liver pathology when injected intraperitoneally into mice. M. deserti plants containing the latter three ketones must be regarded as potentially capable of inducing M. deserti poisoning in stock. A mixture of (-)- deisopropylngaione and (-)- deisopropylepingaione causes both kidney and liver lesions.

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