EurekaMag.com logo
+ Site Statistics
References:
53,517,315
Abstracts:
29,339,501
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Syntheses of s dextro trihexyphenidyl hydrochloride and s levo procyclidine hydrochloride two anticholinergics using s levo 3 cyclohexyl 3 hydroxy 3 phenylpropanoic acid as chiral synthon



Syntheses of s dextro trihexyphenidyl hydrochloride and s levo procyclidine hydrochloride two anticholinergics using s levo 3 cyclohexyl 3 hydroxy 3 phenylpropanoic acid as chiral synthon



Acta Chemica Scandinavica Series B Organic Chemistry & Biochemistry 41(5): 356-361



The absolute configuration of the more active (-)-enantiomer of the anticholinergic trihexyphenidyl hydrochloride has been established as (R) by syntheses of (S)-(+)-procyclidine hydrochloride, whose absolute configuration has been established previously, and (S)-(+)-trihexyphenidyl hydrochloride from the same chiral building block, viz. (S)-(-)-cyclohexyl-3-hydroxy-3-phenylpropanoic acid. Both enantiomers of this chiral synthon were prepared by optical resolution of the corresponding racemate, employing (R)- and (S)-1-phenylethylamine, respectively, as resolving agents.

(PDF 0-2 workdays service: $29.90)

Accession: 006559892

Download citation: RISBibTeXText



Related references

Syntheses of (S)-(+)-trihexyphenidyl hydrochloride and (S)-(+)-procyclidine hydrochloride, two anticholinergics, using (S)-(-)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid as chiral synthon. Acta Chemica Scandinavica. Series B: Organic Chemistry and Biochemistry 41(5): 356-361, 1987

Terpenoid biotransformation in mammals iv biotransformation of dextro longifolene levo caryophyllene levo caryophyllene oxide levo cyclocolorenone dextro nootkatone levo elemol levo abietic acid and dextro dehydroabietic acid in rabbits. Xenobiotica 16(8): 753-768, 1986

The conversion of levo and dextro dihydrocarvone into chiral intermediates for the synthesis of levo polygodial levo warburganal and levo muzigadial. Tetrahedron 45(5): 1447-1452, 1989

Ergot alkaloids the first and five step total syntheses of levo and dextro 6 7 secoagroclavines and the syntheses of levo and dextro 6 nor 6 propyl 6 7 secoagroclavines levo and dextro ksu 1415. Heterocycles (Tokyo) 32(5): 873-878, 1991

Direct high performance liquid chromatographic separation of dextro and levo medetomidine hydrochloride with an alpha 1 acid glycoprotein chiral column. Journal of Chromatography 506: 627-636, 1990

Synthesis of r dextro and s levo 8 hydroxy 2 n n dipropylamino 2 tritium tetralin hydrochloride 8 hydroxy dpat a 5ht 1a receptor agonist. Journal of Labelled Compounds & Radiopharmaceuticals 29(8): 909-918, 1991

Enantiocontrolled syntheses of the cuparene sesquiterpenes levo herbertene dextro beta cuparenone levo debromoaplysin and levo aplysin. Tetrahedron Letters 33(3): 329-332, 1992

General conjugate addition method for the synthesis of enantiomerically pure lignans total synthesis of levo and dextro burseran levo dehydroxycubebin levo trichostin levo cubebin levo 5 ethoxyhinokinin and levo hinokinin. Journal of Organic Chemistry 55(14): 4340-4349, 1990

Biomimetic alkaloid syntheses 15. enantioselective syntheses with epichlorohydrin total syntheses of dextro levo and racemic vindoline and a synthesis of levo vindorosine. Journal of Organic Chemistry 52(3): 347-353, 1987

New chiral polysiloxanes prepared from derivatives of dextro or levo 2 phenyl 3 butenoic acid r 1 hepten 3 ol and r 1 cyclohexyl 2 propen 1 ol. Tetrahedron 43(3): 451-462, 1987

Studies in biomimetic alkaloid syntheses 12. enantioselective total syntheses of levo and dextro vincadifformine and of levo tabersonine. Journal of Organic Chemistry 50(7): 924-929, 1985

Biosynthesis of monoterpenes enantioselectivity in the enzymatic cyclization of dextro and levo linalylpyrophosphate to dextro and levo pinene and dextro and levo camphene. Journal of Biological Chemistry 263(21): 10063-10071, 1988

On the scope of asymmetric nitrile oxide cycloadditions with oppolzer's chiral sultam total syntheses of dextro hepialone levo 1r 3r 5s 1 3 dimethyl 2 9 dioxabicyclo 3.3.1 nonane and levo 1s 7 7 dimethyl 6 8 dioxabicyclo 3.2.1. octane. Journal of Organic Chemistry 55(15): 4585-4595, 1990

Enantio selective route to both dextro and levo enantiomers of quebrachamine using a single chiral synthon. Journal of the Chemical Society Chemical Communications (22): 1153-1155, 1981

An alternative approach to mevinic acid analogues from methyl 3r levo 3 hydroxyhex 5 enoate and an extension to unambiguous syntheses of 6r dextro goniothalamin and 6s levo goniothalamin. Journal of the Chemical Society Perkin Transactions I (3): 519-524, 1991