{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T18:26:58Z","timestamp":1787509618960,"version":"build-2736575974"},"reference-count":30,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2014,10,30]],"date-time":"2014-10-30T00:00:00Z","timestamp":1414627200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"CICYT","award":["CTQ2009-07758"],"award-info":[{"award-number":["CTQ2009-07758"]}]},{"name":"CICYT","award":["CTQ2012-30930"],"award-info":[{"award-number":["CTQ2012-30930"]}]},{"DOI":"10.13039\/501100002809","name":"Generalitat de Catalunya","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100002809","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Institute for Research in Biomedicine Barcelona"}],"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                    New cytotoxic polyketide macrolides named phormidolides\u2005B and C were isolated from a marine sponge of the Petrosiidae family collected off the coast of Pemba (Tanzania). The isolation, structure elucidation, and enantioselective synthesis of three diastereomers of the macrocyclic core is described herein. The described synthetic methodology started from 2\u2010deoxy\u2010\n                    <jats:sc>D<\/jats:sc>\n                    \u2010ribose or 2\u2010deoxy\u2010\n                    <jats:sc>L<\/jats:sc>\n                    \u2010ribose and afforded the desired macrocycles with high enantiomeric purity. The key step of the synthesis is the formation of the\n                    <jats:italic>Z<\/jats:italic>\n                    \u2010trisubstituted double bond using a Julia\u2013Kocienski olefination. The versatility of the synthetic methodology may provide access to other enantiopure macrocycles by making changes in the starting materials or chiral inductors.\n                  <\/jats:p>","DOI":"10.1002\/chem.201404341","type":"journal-article","created":{"date-parts":[[2014,10,30]],"date-time":"2014-10-30T10:59:59Z","timestamp":1414666799000},"page":"150-156","source":"Crossref","is-referenced-by-count":30,"title":["Phormidolides B and C, Cytotoxic Agents from the Sea: Enantioselective Synthesis of the Macrocyclic Core"],"prefix":"10.1002","volume":"21","author":[{"given":"Adriana","family":"Lorente","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro","family":"Gil","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rogelio","family":"Fern\u00e1ndez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carmen","family":"Cuevas","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fernando","family":"Albericio","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mercedes","family":"\u00c1lvarez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,10,30]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2487"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3np70117d"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr3004778"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)79931-X"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-458X(200004)38:4<265::AID-MRC637>3.0.CO;2-#"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo020240s"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo039921t"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ed081p1441"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/c000535e"},{"key":"e_1_2_6_11_2","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/b208078h"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200801117"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00237a008"},{"key":"e_1_2_6_15_2","unstructured":"Identification of each diastereomer was based on 1D\u2010NOE experiments after irradiation over the two diastereotopic protons of the endocyclic4CH2(see the Supporting Information)."},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-98-S(H)72"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.06.014"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.07.125"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01966-2"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00783a034"},{"key":"e_1_2_6_22_2","unstructured":"Changes in the chemical shifts of the signals for1CH3 3CH2and the methyl branch at C6 were indicative for absolute configuration determination."},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1570"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)01902-T"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-836037"},{"key":"e_1_2_6_27_2","unstructured":"Determination of the configuration of the alkene was based on 1D\u2010NOE experiments. Irradiation over the vinyl proton at\u03b4=5.30 and 5.29\u2005ppm of13\u2009aand13\u2009b respectively produced a clear NOE signal on the vinylic CH3singlet signal at\u03b4=1.67 and 1.66\u2005ppm respectively (see the Supporting Information)."},{"key":"e_1_2_6_28_2","first-page":"365","author":"Kocienski P. 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