{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T16:49:28Z","timestamp":1790009368229,"version":"4.0.1"},"reference-count":167,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2014,11,3]],"date-time":"2014-11-03T00:00:00Z","timestamp":1414972800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"MPG"},{"name":"Fonds der Chemischen Industrie"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2015,1,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Lactones are known to react with the reagent generated in situ from CCl\n                    <jats:sub>4<\/jats:sub>\n                    and PPh\n                    <jats:sub>3<\/jats:sub>\n                    in a Wittig\u2010type fashion to give\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010dichloro\u2010olefin derivatives. Such compounds are now shown to undergo reductive alkylation on treatment with organolithium reagents RLi to furnish acetylene derivatives bearing the substituent R at their termini (R=Me,\n                    <jats:italic>n<\/jats:italic>\n                    \u2010,\n                    <jats:italic>sec<\/jats:italic>\n                    \u2010,\n                    <jats:italic>tert<\/jats:italic>\n                    \u2010alkyl, silyl); the reaction can be catalyzed with either Cu(acac)\n                    <jats:sub>2<\/jats:sub>\n                    or Fe(acac)\n                    <jats:sub>3<\/jats:sub>\n                    \/1,2\u2010diaminobenzene. Two alkynol derivatives prepared in this way from readily accessible lactone precursors served as the key building blocks for the total syntheses of the cytotoxic marine macrolides tulearin\u2005A (\n                    <jats:bold>1<\/jats:bold>\n                    ) and C (\n                    <jats:bold>2<\/jats:bold>\n                    ). The assembly of these fragile targets hinged upon ring closing alkyne metathesis (RCAM) followed by a formal\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010reduction of the resulting cycloalkynes via\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010hydrosilylation\/protodesilylation.\n                  <\/jats:p>","DOI":"10.1002\/chem.201404873","type":"journal-article","created":{"date-parts":[[2014,11,3]],"date-time":"2014-11-03T16:04:51Z","timestamp":1415030691000},"page":"219-227","source":"Crossref","is-referenced-by-count":41,"title":["A New Method for the Preparation of Non\u2010Terminal Alkynes: Application to the Total Syntheses of Tulearin\u2005A and C"],"prefix":"10.1002","volume":"21","author":[{"given":"Konrad","family":"Lehr","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saskia","family":"Schulthoff","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshihiro","family":"Ueda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ronaldo","family":"Mariz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucie","family":"Leseurre","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbara","family":"Gabor","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alois","family":"F\u00fcrstner","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,11,3]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204513"},{"key":"e_1_2_6_1_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204513"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201207772"},{"key":"e_1_2_6_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201207772"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201302320"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404166"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201400605"},{"key":"e_1_2_6_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201400605"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol702221v"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.04.028"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900936t"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.02.052"},{"key":"e_1_2_6_10_2","unstructured":"\u00a0"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar000114f"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G"},{"key":"e_1_2_6_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000901)112:17<3140::AID-ANGE3140>3.0.CO;2-G"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500369"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500369"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature06351"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc10464k"},{"key":"e_1_2_6_16_2","unstructured":"Metathesis in Natural Product Synthesis: Strategies Substrates and Catalysts (Eds.: J. Cossy S. Arseniyadis C. Meyer) Wiley\u2010VCH Weinheim 2010."},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1229713"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980703)37:12<1734::AID-ANIE1734>3.0.CO;2-6"},{"key":"e_1_2_6_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980619)110:12<1758::AID-ANGE1758>3.0.CO;2-I"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja992074k"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20011217)7:24<5299::AID-CHEM5299>3.0.CO;2-X"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0103726"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106117"},{"key":"e_1_2_6_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106117"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199607501"},{"key":"e_1_2_6_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961080722"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(81)80144-X"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00098a039"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1991-20806"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030640v"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200165q"},{"key":"e_1_2_6_30_2","unstructured":"Such lactone\u2010derived dichloro\u2010olefins tend to decompose upon storage; however most of the compounds described herein can be kept in a refrigerator under Ar for several days."},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39930000137"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-985585"},{"key":"e_1_2_6_34_2","unstructured":"\u00a0"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19800000410"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol052685j"},{"key":"e_1_2_6_37_2","unstructured":"Other (co)solvents investigated led to dramatic losses; hexane retards the reaction whereas the use of CH2Cl2 NMP or DMPU as additives furnished intractable mixtures."},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/a709111g"},{"key":"e_1_2_6_39_2","unstructured":"This conclusion is supported by a control experiment using 1\u2010chloro\u20101\u2010heptyne: as expected treatment with MeLi merely furnished 1\u2010heptyne after aqueous work\u2010up which shows that a lithium acetylide was formed but not trapped by the methyl chloride generated in situ."},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980302)37:4<430::AID-ANIE430>3.0.CO;2-5"},{"key":"e_1_2_6_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980216)110:4<444::AID-ANGE444>3.0.CO;2-J"},{"key":"e_1_2_6_41_2","unstructured":"For pioneering studies on the reaction of alkali metal vinylidene species with nucleophiles see:"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19671000630"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00329a084"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00283a064"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00055a004"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00224a049"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.76.2009"},{"key":"e_1_2_6_48_2","unstructured":"For DFT\u2010studies indicating a low\u2010lying LUMO see:"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00334a001"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.07.030"},{"key":"e_1_2_6_51_2","unstructured":"X\u2010ray structures of 1\u2010chloro\u20101\u2010lithio (magnesio)ethene derivatives indicate considerable rehydridization of the vinylidene C atom (higher s\u2010character) and a 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