{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T14:12:43Z","timestamp":1788444763990,"version":"build-2803163510"},"reference-count":27,"publisher":"American Chemical Society (ACS)","issue":"8","license":[{"start":{"date-parts":[[2020,4,2]],"date-time":"2020-04-02T00:00:00Z","timestamp":1585785600000},"content-version":"vor","delay-in-days":2,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccby_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/P030742\/1"],"award-info":[{"award-number":["EP\/P030742\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000761","name":"Imperial College London","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100000761","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000943","name":"Commonwealth Scientific and Industrial Research Organisation","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100000943","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,4,17]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated \u03946,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.<\/jats:p>","DOI":"10.1021\/acs.orglett.0c00935","type":"journal-article","created":{"date-parts":[[2020,3,31]],"date-time":"2020-03-31T15:10:04Z","timestamp":1585667404000},"page":"3176-3179","source":"Crossref","is-referenced-by-count":5,"title":["Relay Cross Metathesis for the Iterative Construction\nof Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic\nRelevance to the Bromophycolides"],"prefix":"10.1021","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8302-5283","authenticated-orcid":true,"given":"Karim A.","family":"Bahou","sequence":"first","affiliation":[{"name":"Imperial College London , , ,","place":["London, United Kingdom, W12 0BZ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4161-7256","authenticated-orcid":true,"given":"D. Christopher","family":"Braddock","sequence":"additional","affiliation":[{"name":"Imperial College London , , ,","place":["London, United Kingdom, W12 0BZ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adam G.","family":"Meyer","sequence":"additional","affiliation":[{"name":"Jerry Price Laboratory , , Research Way , , ,","place":["Clayton, Victoria, Australia, 3168"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7805-8630","authenticated-orcid":true,"given":"G. Paul","family":"Savage","sequence":"additional","affiliation":[{"name":"Jerry Price Laboratory , , Research Way , , ,","place":["Clayton, Victoria, Australia, 3168"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,3,31]]},"reference":[{"key":"2026090309182213700_cit1","volume-title":"Nature\u2019s Chemicals:\nThe Natural Products that Shaped Our World","author":"Firn","year":"2010"},{"key":"2026090309182213700_cit2","doi-asserted-by":"crossref","DOI":"10.1002\/9783527609949","volume-title":"Terpenes:\nFlavors, Fragrances, Pharmaca, Pheromones","author":"Breitmaier","year":"2006"},{"key":"2026090309182213700_cit3","unstructured":"For a pictorial \u201cTop\npharmaceuticals\u201d, see: http:\/\/njardarson.lab.arizona.edu\/content\/top-pharmaceuticals-poster (2019-06-11)."},{"key":"2026090309182213700_cit4","article-title":"Isoprenoids Including\nCartenoids and Steroids","volume-title":"Comprehensive\nNatural Product Chemistry","author":"Barton","year":"1999"},{"key":"2026090309182213700_cit5","doi-asserted-by":"publisher","first-page":"131","DOI":"10.1016\/j.abb.2010.09.028","article-title":"Enzymes\nof the mevalonate pathway of isoprenoid biosynthesis","volume":"505","author":"Miziorko","year":"2011","journal-title":"Arch. 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C.Imperial College HPC Data Repository, 2019. 10.14469\/hpc\/6103 (accessed 2020-01-29)."},{"key":"2026090309182213700_cit26","unstructured":"The first version of this article\nwas deposited to the ChemRxiv preprint server on June 13, 2019. 10.26434\/chemrxiv.8267837.v1."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.0c00935","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/22\/8\/3176\/67247799\/acs.orglett.0c00935.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/22\/8\/3176\/67247799\/acs.orglett.0c00935.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T13:18:29Z","timestamp":1788441509000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/22\/8\/3176\/1497885\/Relay-Cross-Metathesis-for-the-Iterative"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3,31]]},"references-count":27,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2020,3,31]]},"published-print":{"date-parts":[[2020,4,17]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.0c00935","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,3,31]]}}}