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1An Efficient Enantioselective Synthesis of the D1 Agonist (5Ar,11bs)-4,5,5A,6,7,11b-hexahydro-2-propyl-3-thia- 5-Azacyclopenta[c]phenanthrene-9,10-diol (A-86929)

Paul P. Ehrlich,Jeffrey W. Ralston,Michael R. Michaelides

(5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propyl-3-thia-5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929, 1), a potent selective dopamine D1 agonist, was synthesized enantioselectively from d-aspartic acid. Key features of the 10-step synthesis are the following: (1) there is no chromatography required; (2) formation of 15 occurs in >99% ee; (3) the electrophilic cyclization to provide the desired trans stereochemisry in 18 is achieved with no loss of enantiomeric integrity.

1997The Journal of organic chemistry（1997）引用：38

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2Formal Asymmetric Synthesis Of Dihydrexidine

Jw Ralston,Pp Ehrlich, Nc Monberg

1997ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY（1997）

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3Enantioselective Synthesis Of The Trans Benz[E]Isoindole Ring System

Pp Ehrlich,Jw Ralston,Md Meyer

1997ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY（1997）

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4Synthesis and Pharmacological Characterization of 3-[2-((3ar,9br)-cis-6-methoxy-2,3,3a,4,5,9b-hexahydro-1h-benz[e]isoindol -2-yl)ethyl]pyrido-[3',4':4,5]Thieno[3,2-d]pyrimidine-2,4(1h,3h)-dione (A-131701): A Uroselective Alpha(1a) Adrenoceptor Antagonist for the Symptomatic Treatment of Benign Prostatic Hyperplasia

MD Meyer,RJ Altenbach,FZ Basha,WA Carroll,I Drizin,SW Elmore,PP Ehrlich,SA Lebold,K Tietje,KB Sippy,MD Wendt,DJ Plata,

ADVERTISEMENT RETURN TO ISSUELetterNEXTSynthesis and Pharmacological Characterization of 3-[2-((3aR,9bR)-cis-6-Methoxy- 2,3,3a,4,5,9b-hexahydro-1H- benz[e]isoindol-2-yl)ethyl]pyrido[3',4':4,5]thieno[3,2-d]pyrimidine- 2,4(1H,3H)-dione (A-131701): A Uroselective α1A Adrenoceptor Antagonist for the Symptomatic Treatment of Benign Prostatic Hyperplasia 1Michael D. Meyer, Robert J. Altenbach, Fatima Z. Basha, William A. Carroll, Irene Drizin, Steven W. Elmore, Paul P. Ehrlich, Suzanne A. Lebold, Karin Tietje, Kevin B. Sippy, Michael D. Wendt, Daniel J. Plata, Fred Plagge, Steven A. Buckner, Michael E. Brune, Arthur A. Hancock, and James F. KerwinView Author Information Neurological and Urological Diseases Research, D-47C, and Process Research, D-45L, Abbott Laboratories, Abbott Park, Illinois 60064-3500 Cite this: J. Med. Chem. 1997, 40, 20, 3141–3143Publication Date (Web):September 26, 1997Publication History Received2 June 1997Published online26 September 1997Published inissue 1 September 1997https://pubs.acs.org/doi/10.1021/jm970364ahttps://doi.org/10.1021/jm970364arapid-communicationACS PublicationsCopyright © 1997 American Chemical SocietyRequest reuse permissionsArticle Views508Altmetric-Citations16LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Amines,Anatomy,Antagonists,Receptors,Selectivity Get e-Alerts

1997Journal of Medicinal Chemistry（1997）引用：26

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5ChemInform Abstract: an Efficient Enantioselective Synthesis of the D1 Agonist (5ar,11bs)‐4, 5,5a,6,7,11b‐hexahydro‐2‐propyl‐3‐thia‐5‐azacyclopenta(c)phenanthrene‐ 9,10‐diol (A‐86929).

P. P. EHRLICH,J. W. RALSTON,M. R. MICHAELIDES

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

1997ChemInform（1997）引用：8

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6Discovery Of Novel Potent And Selective Alpha(1a) Adrenoceptor Antagonists For The Symptomatic Treatment Of Benign Prostatic Hyperplasia (Bph)

Md Meyer,Rj Altenbach,Fz Basha,Wa Carroll,I Drizin,Pp Ehrlich,Sw Elmore,Sa Lebold,Kb Sippy,K Tietje,Md Wendt,Aa Hancock,

1997ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY（1997）

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7Binding And Functional-Activity Of Novel Conformationally Restrained Dopamine Agonists And Antagonists Of The Benzazepine Series

Pp Ehrlich, Jr Campbell,Cw Lin,B Bianchi,E Roberts

1995ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY（1995）

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8N-Methyl-5-(R)-Phenylhexahydrobenz(H)Isoquinoline - A Novel Lead for the Development of Potent and Selective Da D1 Receptor Agonists

PP EHRLICH,S DIDOMENICO,CW LIN,B BIANCHI,M STASHKO,DR BRITTON,J MIKUSA,L MAHAN,K ASIN,L HODGES,A NIKKEL,T MILLER,

1995ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY

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9Synthesis, Conformation, Crystal Structures and DNA Cleavage Abilities of Tetracyclic Analogs of Quinocarcin

RM WILLIAMS,T GLINKA,R GALLEGOS,PP EHRLICH, ME FLANAGAN,H COFFMAN,G PARK

Two totally synthetic, racemic analogs of quinocarcin have been designed and their crystal structures determined. Both substances effect the modest cleavage of plasmid DNA. Alteration of the conformation of the reactive oxazolidine fused to the piperazine ring by selecting the stereochemistry at C-11a through synthesis drastically attenuates the relative ability of these substances to cleave DNA.

1991TETRAHEDRON（1991）引用：32

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10A New Synthetic Approach to 1-(Hydroxymethyl)-8-methoxy-1,2,3,4-tetrahydroisoquinolin-4-one

RM WILLIAMS,PP EHRLICH,WX ZHAI,J HENDRIX

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA new synthetic approach to 1-(hydroxymethyl)-8-methoxy-1,2,3,4-tetrahydroisoquinolin-4-oneRobert M. Williams, Paul P. Ehrlich, Weixu Zhai, and James HendrixCite this: J. Org. Chem. 1987, 52, 12, 2615–2617Publication Date (Print):June 1, 1987Publication History Published online1 May 2002Published inissue 1 June 1987https://pubs.acs.org/doi/10.1021/jo00388a056https://doi.org/10.1021/jo00388a056research-articleACS PublicationsRequest reuse permissionsArticle Views578Altmetric-Citations37LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

1987The Journal of Organic Chemistry（1987）引用：65

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11ChemInform Abstract: A New Synthetic Approach to 1‐(Hydroxymethyl)‐8‐methoxy‐1,2,3,4‐tetrahydroisoquinolin‐4‐one.

R. M. WILLIAMS,P. P. EHRLICH,W. ZHAI,J. HENDRIX

AbstractCoupling of the lithiated anisole (I) with the protected glycolic acid amide (II) gives the benzyloxyacetophenone (III) which is reductively aminated and then deprotected to yield 2‐(o‐methoxyphenyl)‐2‐aminoethanol (V).

1987ChemInform（1987）引用：33

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12Synthetic Approach To Quinocarcin

Pp Ehrlich,J Hendrix,Wx Zhai,Rm Williams

1987ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY（1987）引用：22

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