An efficient stereospecific synthesis of 3?-deoxythymidine has been achieved, starting from D-xylose. The key step of the synthesis involved the NBS promoted conversion of 5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-D-ribose diethyl dithioacetal (4) into the 1-O-acetyl-5-O-benzoyl-2,3-di-S-ethyl-2,3-dithio-?-D-ribofuranose (5) followed by the stereospecific coupling of the intermediate 5 with silylated thymine, in the presence of ethylaluminium dichloride as the catalyst.

The key chiral synthon in a novel synthesis of (-)-allo-muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion via the 4-O-benzoyl derivatives of starting 2,5-anhydro-3,5-di-O-methanesulfonyl-L-idose ethylene acetal (2a) into 2,5-anhydro-3,6-dideoxy-L-lyxo-hexose ethylene acetal (4b). The intermediate 4b was efficiently converted into the chiral synthon 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-arabino-hexose (4c) by Mitsunobu reaction.

Two independent routes towards (2 S )-3-(indol-3-yl)propane-1,2-diol ( 11 ) were achieved starting from 3,5-di- O -acetyl-1,2- O -cyclohexylidene-α-D-xylofuranose ( 1 ). Ethanethiolysis of 1 afforded acyclic diethyl dithioacetal 2 which was further O -deacetylated to give 3 . Selective benzoylation of 3 gave 5- O -benzoyl derivative 4 . Treatment of 4 with N -bromosuccinimide in methanol gave methyl furanoside 5 which was further desulfurized over Raney nickel to afford 6 . An acid hydrolysis of 6 gave hemiacetal 7 which upon treatment with phenylhydrazine, according to standard Fischer indolization procedure, yielded a mixture of chiral indoles 10 . O -Debenzoylation of 10 gave the crystalline diol 11 . A more efficient route towards the chiral indole 11 included the initial dethioacetalation of 2 into dimethyl acetal 8 which was further desulfurized over Raney nickel to give the corresponding 2,3-dideoxy derivative 9 . Direct Fischer indolization of 9 with phenylhydrazine, followed by O -deacetylation of intermediate 12 , afforded the expected indole 11 in good yield.

C20H36O5S5, M(r) = 516.82, monoclinic, P2(1), a = 8.670 (1), b = 17.149 (1), c = 9.224 (1) angstrom, beta = 95.88 (1)-degrees, V = 1364.2 (3) angstrom3, Z = 2, D(m) = 1.26, D(x) = 1.27 g cm-3, lambda(Cu Kalpha) = 1.54178 angstrom, mu = 40.8 cm-1 F(000) = 552.0, T = 296 K, final R = 0.066, wR = 0.065 for 3478 observed reflections. The purpose of the structure determination was to establish the position of the substituents and the molecular conformation of the title compound (2) obtained by acid catalyzed ethanethiolysis of 3,4-di-O-acetyl-6-S-acetyl-1,2-isopropylidene-6-thio-alpha-D-glucofuranose (1). Since the product (2) was planned as a starting synthone in a sequence of reactions, its stereochemistry was of essential importance to us.

The structure of o-amicetose (2,3,6-trideoxy-o-evthro-hexose, l), a constituent of the antibiotic amicetin’, was proved first by synthesis from o-gluca12. Since then, numerous syntheses of o-amicetose and related sugars have been described3, and that by Bethel1 and Ferrier4 is relevant to the work now reported. The starting material for their synthesis4 was 3-0-benzoyl-1,2 : 5,6-di-O-isopropylidene-o-D-glucofuranose (3) and the key step involved ethanethiolysis of 3 to give the tetrathio derivative 7 in a yield of _ 40%. The postulated precursor of 7, the acyclic D-&I intermediate 8, was assumed on the basis of earlier work@. We now report on the acid-catalysed ethanethiolysis of 3,5-di-0-acetyl-6-Sacetyl-1,2-0-isopropylidene-6-thio-cu-D_ranose (5) and 3,5,6-tri-O-benzoyl1,2-O-isopropylidene+o-glucofuranose7 (6). In parallel with the earlier work5T6, 10 was main product (> 90% from 5).

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.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAlkaloids of Delphinium staphisagria. The structure and stereochemistry of delphisine, neoline, chasmanine, and homochasmanineS. W. Pelletier, Z. Djarmati, S. Lajsic, and Wilson H. De CampCite this: J. Am. Chem. Soc. 1976, 98, 9, 2617–2625Publication Date (Print):April 1, 1976Publication History Published online1 May 2002Published inissue 1 April 1976https://pubs.acs.org/doi/10.1021/ja00425a035https://doi.org/10.1021/ja00425a035research-articleACS PublicationsRequest reuse permissionsArticle Views276Altmetric-Citations38LEARN 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 Get e-Alerts

AbstractAnhand der Röntgen‐ Spektralanalyse, NMR‐Spektren (Abbildung) und chemischer Untersuchungen werden für Delphisin (Ia) die absolute Konfiguration 1S, 4S, 5R, 6R, 7R, 8R, 9R, IOR, 11S, 13R, 14S, 16S, 17R, die Wannenform für den Ring A, sowie die Zugehörigkeit zu dem Typ der Aconitin‐Alkaloide ermittelt.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe structures of staphigine and staphirine. Two novel bisditerpene alkaloids from Delphinium staphisagriaS. William Pelletier, Naresh V. Mody, Zoltan Djarmati, and Stevan D. LajsicCite this: J. Org. Chem. 1976, 41, 18, 3042–3044Publication Date (Print):September 1, 1976Publication History Published online1 May 2002Published inissue 1 September 1976https://pubs.acs.org/doi/10.1021/jo00880a032https://doi.org/10.1021/jo00880a032research-articleACS PublicationsRequest reuse permissionsArticle Views110Altmetric-Citations14LEARN 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

Chemischer InformationsdienstVolume 6, Issue 8 Natural Products ChemInform Abstract: STRUCTURE OF NEOLINE, CHASMANINE, AND HOMOCHASMANINE S. W. PELLETIER, S. W. PELLETIERSearch for more papers by this authorZ. DJARMATI, Z. DJARMATISearch for more papers by this authorS. D. LAJSIC, S. D. LAJSICSearch for more papers by this author S. W. PELLETIER, S. W. PELLETIERSearch for more papers by this authorZ. DJARMATI, Z. DJARMATISearch for more papers by this authorS. D. LAJSIC, S. D. LAJSICSearch for more papers by this author First published: February 25, 1975 https://doi.org/10.1002/chin.197508469AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume6, Issue8February 25, 1975 RelatedInformation

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNaturally occurring terpenes. Synthesis of (+)- and (+-)-14,15-bisnor-8.alpha.-hydroxylabd-11(E)-en-13-one, (+)-drimane-8,11-diol, and (-)-drimenolS. William Pelletier, Stevan Lajsic, Yasuo Ohtsuka, and Zoltan DjarmatiCite this: J. Org. Chem. 1975, 40, 11, 1607–1609Publication Date (Print):May 1, 1975Publication History Published online1 May 2002Published inissue 1 May 1975https://pubs.acs.org/doi/10.1021/jo00899a019https://doi.org/10.1021/jo00899a019research-articleACS PublicationsRequest reuse permissionsArticle Views232Altmetric-Citations30LEARN 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

The cycloaddition of diazoalkanes, diazoesters and diazoketones to 2(5H)-furanones followed by thermal decomposition of the respective adducts is shown to provide a general method for the preparation of a variety of alkylated 2(5H)-furanones. Reduction of the latter compounds with diisobutylaluminum hydride affords the corresponding substituted furans in good yield.

AbstractDie Furanone (I) addieren die Diazoalkane (II) unter praktisch quantitativer Bildung der Pyrazolincarbonsäurelactone (III), die beim Erhitzen in Dioxan in die Furanone (IV) übergehen.

Chemischer InformationsdienstVolume 6, Issue 8 Physical Organic Chemistry ChemInform Abstract: STRUCTURE AND ABSOLUTE CONFIGURATION OF DELPHISINE, A NEW DITERPENE ALKALOID FROM DELPHINIUM STAPHISAGRIA S. W. PELLETIER, S. W. PELLETIERSearch for more papers by this authorW. H. DE CAMP, W. H. DE CAMPSearch for more papers by this authorS. D. LAJSIC, S. D. LAJSICSearch for more papers by this authorZ. DJARMATI, Z. DJARMATISearch for more papers by this authorA. H. KAPADI, A. H. KAPADISearch for more papers by this author S. W. PELLETIER, S. W. PELLETIERSearch for more papers by this authorW. H. DE CAMP, W. H. DE CAMPSearch for more papers by this authorS. D. LAJSIC, S. D. LAJSICSearch for more papers by this authorZ. DJARMATI, Z. DJARMATISearch for more papers by this authorA. H. KAPADI, A. H. KAPADISearch for more papers by this author First published: February 25, 1975 https://doi.org/10.1002/chin.197508098AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume6, Issue8February 25, 1975 RelatedInformation

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStructure of neoline, chasmanine, and homochasmanineS. W. Pelletier, Z. Djarmati, and S. LajsicCite this: J. Am. Chem. Soc. 1974, 96, 25, 7817–7818Publication Date (Print):December 1, 1974Publication History Published online1 May 2002Published inissue 1 December 1974https://pubs.acs.org/doi/10.1021/ja00832a038https://doi.org/10.1021/ja00832a038research-articleACS PublicationsRequest reuse permissionsArticle Views143Altmetric-Citations14LEARN 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

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStructure and absolute configuration of delphisine. New diterpene alkaloid from Delphinium staphisagriaS. W. Pelletier, W. H. DeCamp, S. Lajsic, Z. Djarmati, and A. H. KapadiCite this: J. Am. Chem. Soc. 1974, 96, 25, 7815–7817Publication Date (Print):December 1, 1974Publication History Published online1 May 2002Published inissue 1 December 1974https://doi.org/10.1021/ja00832a037RIGHTS & PERMISSIONSArticle Views80Altmetric-Citations14LEARN 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 InReddit PDF (318 KB) Get e-Alerts Get e-Alerts

AbstractBei der Umsetzung der Butenolide (I) mit Diazomethan (II) entstehen die Addukte (III), die thermisch zu den methylierten Butenoliden (IV) gespalten werden.