{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T13:17:10Z","timestamp":1792675030603,"version":"4.5.0"},"reference-count":37,"publisher":"American Association for the Advancement of Science (AAAS)","issue":"6148","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Science"],"published-print":{"date-parts":[[2013,8,23]]},"abstract":"<jats:title>Ingenol Ingenuity<\/jats:title>\n                  <jats:p>\n                    The diterpenoid i ngenol is the core structure of a topical drug recently commercialized to treat actinic keratosis, a precancerous skin condition. Sourcing the compound from the\n                    <jats:italic>Euphorbia<\/jats:italic>\n                    plants that produce it is relatively inefficient, so\n                    <jats:bold>\n                      J\u00f8rgensen\n                      <jats:italic>et al.<\/jats:italic>\n                    <\/jats:bold>\n                    (p.\n                    <jats:related-article xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"doi\" issue=\"6148\" page=\"878\" related-article-type=\"in-this-issue\" vol=\"341\" xlink:href=\"10.1126\/science.1241606\">878<\/jats:related-article>\n                    , published online 1 August) devised a chemical synthesis starting from the comparatively simple and inexpensive monoterpene chiral (+)-3-carene. The synthetic sequence involves 14 steps\u2014less than half as long as prior chemical routes to the target\u2014and relies on a two-stage approach, inspired by the posited biosynthetic pathway, in which preliminary assembly of the fused ring framework precedes hydroxylation of the periphery.\n                  <\/jats:p>","DOI":"10.1126\/science.1241606","type":"journal-article","created":{"date-parts":[[2013,8,2]],"date-time":"2013-08-02T01:07:22Z","timestamp":1375405642000},"page":"878-882","source":"Crossref","is-referenced-by-count":341,"title":["14-Step Synthesis of (+)-Ingenol from (+)-3-Carene"],"prefix":"10.1126","volume":"341","author":[{"given":"Lars","family":"J\u00f8rgensen","sequence":"first","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Steven J.","family":"McKerrall","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christian A.","family":"Kuttruff","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felix","family":"Ungeheuer","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jakob","family":"Felding","sequence":"additional","affiliation":[{"name":"External Discovery, LEO Pharma A\/S, Industriparken 55, 2750 Ballerup, Denmark."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Phil S.","family":"Baran","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd1657"},{"key":"e_1_3_2_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-7799(02)02080-2"},{"key":"e_1_3_2_4_2","unstructured":"P. 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