{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T07:54:36Z","timestamp":1790754876225,"version":"4.1.0"},"reference-count":23,"publisher":"American Chemical Society (ACS)","issue":"21","license":[{"start":{"date-parts":[[2025,5,15]],"date-time":"2025-05-15T00:00:00Z","timestamp":1747267200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-2247315"],"award-info":[{"award-number":["CHE-2247315"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014221","name":"Heritage Medical Research Institute","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100014221","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2025,5,30]]},"DOI":"10.1021\/acs.orglett.5c01332","type":"journal-article","created":{"date-parts":[[2025,5,15]],"date-time":"2025-05-15T10:18:21Z","timestamp":1747304301000},"page":"5390-5393","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis of the Pentacyclic Core of Sanguinone B Enabled by Alkyne Functionalization"],"prefix":"10.1021","volume":"27","author":[{"given":"Jonathan","family":"Farhi","sequence":"first","affiliation":[{"name":"The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering","place":["Pasadena, United States"]},{"name":"California Institute of Technology","place":["Pasadena, United States"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samir P.","family":"Rezgui","sequence":"additional","affiliation":[{"name":"The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering","place":["Pasadena, United States"]},{"name":"California Institute of Technology","place":["Pasadena, United States"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-6002-6276","authenticated-orcid":true,"given":"Hao","family":"Yu","sequence":"additional","affiliation":[{"name":"The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering","place":["Pasadena, United States"]},{"name":"California Institute of Technology","place":["Pasadena, United States"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9837-1528","authenticated-orcid":true,"given":"Brian M.","family":"Stoltz","sequence":"additional","affiliation":[{"name":"The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering","place":["Pasadena, United States"]},{"name":"California Institute of Technology","place":["Pasadena, United States"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,5,15]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100435g"},{"key":"ref2\/cit2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c06578"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c10212"},{"key":"ref4\/cit4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c00350"},{"key":"ref5\/cit5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315284"},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1021\/ja00032a036"},{"key":"ref7\/cit7","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80375-0"},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1021\/jo9815397"},{"key":"ref9\/cit9","doi-asserted-by":"publisher","DOI":"10.1021\/jo961743z"},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c11897"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1021\/np070179s"},{"key":"ref12\/cit12","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b00942"},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC02981J"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.1021\/ja901573x"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303669"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02858"},{"key":"ref17\/cit17","unstructured":"Intriguingly,\nupon treatment\nof\n                      N-\n                      tosylated tricycle\n                      S6\n                      with these\nsame conditions, we did not observe conversion to ketone\n                      6\n                      and instead observed depropargylated secondary aniline\n                      S5\n                      as the sole product. We hypothesize that the observed depropargylation\nis due to the trapping of the intermediate ketene by trace water or\nthe oxidant, followed by a retro-aza-Michael reaction."},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1021\/ja01487a058"},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1055\/s-0040-1706020"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202204015"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1021\/ja0432968"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705940"},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.2174\/138527209789630497"}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.5c01332","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.5c01332","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,15]],"date-time":"2025-12-15T18:09:07Z","timestamp":1765822147000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.orglett.5c01332"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,15]]},"references-count":23,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2025,5,30]]}},"alternative-id":["10.1021\/acs.orglett.5c01332"],"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.5c01332","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,15]]}}}