ChemInform Abstract: SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF OPTICALLY ACTIVE WIELAND-MIESCHER KETONE ANALOGS BEARING AN ANGULAR PROTECTED HYDROXYMETHYL GROUP

1985 ◽  
Vol 16 (38) ◽  
Author(s):  
Y. TAMAI ◽  
Y. MIZUTANI ◽  
H. HAGIWARA ◽  
H. UDA ◽  
N. HARADA
Keyword(s):  
Optically Active ◽  
Hydroxymethyl Group ◽  
Absolute Stereochemistry

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.

scholarly journals New HSV-1 Anti-Viral 1′-Homocarbocyclic Nucleoside Analogs with an Optically Active Substituted Bicyclo[2.2.1]Heptane Fragment as a Glycoside Moiety

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2446 ◽  
Author(s):  
Tănase ◽  
Drăghici ◽  
Hanganu ◽  
Pintilie ◽  
Maganu ◽  
...  
Keyword(s):  
Chlorine Atom ◽  
Yellow Fever ◽  
Nucleoside Analogs ◽  
Optically Active ◽  
Mitsunobu Reaction ◽  
Hydroxyl Group ◽  
Hydroxymethyl Group ◽  
Sugar Moiety ◽  
Pyrimidine Analogs ◽  
Hsv 1

New 1′-homocarbanucleoside analogs with an optically active substituted bicyclo[2.2.1]heptane skeleton as sugar moiety were synthesized. The pyrimidine analogs with uracil, 5-fluorouracil, thymine and cytosine and key intermediate with 6-chloropurine (5) as nucleobases were synthesized by a selective Mitsunobu reaction on the primary hydroxymethyl group in the presence of 5-endo-hydroxyl group. Adenine and 6-substituted adenine homonucleosides were obtained by the substitution of the 6-chlorine atom of the key intermediate 5 with ammonia and selected amines, and 6-methoxy- and 6-ethoxy substituted purine homonucleosides by reaction with the corresponding alkoxides. No derivatives appeared active against entero, yellow fever, chikungunya, and adeno type 1viruses. Two compounds (6j and 6d) had lower IC50 (15 ± 2 and 21 ± 4 µM) and compound 6f had an identical value of IC50 (28 ± 4 µM) to that of acyclovir, suggesting that the bicyclo[2.2.1]heptane skeleton could be further studied to find a candidate for sugar moiety of the nucleosides.

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
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