Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural(2S, 3S)-Tartaric Acid

The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural(2S, 3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the ad...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1991/10/25, Vol.39(10), pp.2550-2555
Hauptverfasser:	KOBAYASHI, Yuko, MATSUMOTO, Teruyo, TAKEMOTO, Yoshiji, NAKATANI, Kazuhiko, ITO, Yoshio, KAMIJO, Tetsuhide, HARADA, Hiromu, TERASHIMA, Shiro
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Sprache:	eng
Schlagworte:	1, 2, 3-amino diol 1, 2-amino alcohol C-terminal component cerium(III) chloride chelation control epoxide formation epoxide opening Grignard reagent oxidative cleavege renin inhibitor
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container_title	Chemical & pharmaceutical bulletin
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creator	KOBAYASHI, Yuko MATSUMOTO, Teruyo TAKEMOTO, Yoshiji NAKATANI, Kazuhiko ITO, Yoshio KAMIJO, Tetsuhide HARADA, Hiromu TERASHIMA, Shiro
description	The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural(2S, 3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. The addition product could be elaborated into three types of C-terminal components of renin inhibitors by employing oxidative cleavage of the 1, 2-diol moiety, epoxide formation with inversion of configuration, and epoxide opening with a nucleophile.
doi_str_mv	10.1248/cpb.39.2550
format	Article
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A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. The addition product could be elaborated into three types of C-terminal components of renin inhibitors by employing oxidative cleavage of the 1, 2-diol moiety, epoxide formation with inversion of configuration, and epoxide opening with a nucleophile.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.39.2550</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>1, 2, 3-amino diol ; 1, 2-amino alcohol ; C-terminal component ; cerium(III) chloride ; chelation control ; epoxide formation ; epoxide opening ; Grignard reagent ; oxidative cleavege ; renin inhibitor</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1991/10/25, Vol.39(10), pp.2550-2555</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1991</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4700-d98319f39d7fd1927c420b213dd05b3c2bd77aa5316091ffc66fba7601d33c8b3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,4022,27922,27923,27924</link.rule.ids></links><search><creatorcontrib>KOBAYASHI, Yuko</creatorcontrib><creatorcontrib>MATSUMOTO, Teruyo</creatorcontrib><creatorcontrib>TAKEMOTO, Yoshiji</creatorcontrib><creatorcontrib>NAKATANI, Kazuhiko</creatorcontrib><creatorcontrib>ITO, Yoshio</creatorcontrib><creatorcontrib>KAMIJO, Tetsuhide</creatorcontrib><creatorcontrib>HARADA, Hiromu</creatorcontrib><creatorcontrib>TERASHIMA, Shiro</creatorcontrib><title>Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural(2S, 3S)-Tartaric Acid</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural(2S, 3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. 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Pharm. Bull.</addtitle><date>1991</date><risdate>1991</risdate><volume>39</volume><issue>10</issue><spage>2550</spage><epage>2555</epage><pages>2550-2555</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>The addition reaction of cyclohexylmethylmagnesium bromide with the imine prepared from unnatural(2S, 3S)-tartaric acid was found to proceed in a highly stereoselective manner in the presence of cerium(III) chloride. A chelation-controlled mechanism could explain the stereochemical outcome of the addition reaction. The addition product could be elaborated into three types of C-terminal components of renin inhibitors by employing oxidative cleavage of the 1, 2-diol moiety, epoxide formation with inversion of configuration, and epoxide opening with a nucleophile.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.39.2550</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record>
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source	J-STAGE Free; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry
subjects	1, 2, 3-amino diol 1, 2-amino alcohol C-terminal component cerium(III) chloride chelation control epoxide formation epoxide opening Grignard reagent oxidative cleavege renin inhibitor
title	Novel Synthesis of Three Types of C-Terminal Components of Renin Inhibitors from Unnatural(2S, 3S)-Tartaric Acid
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