{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T13:56:09Z","timestamp":1790949369030,"version":"4.1.0"},"reference-count":44,"publisher":"American Chemical Society (ACS)","issue":"39","license":[{"start":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T00:00:00Z","timestamp":1790035200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T00:00:00Z","timestamp":1790035200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T00:00:00Z","timestamp":1790035200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100003579","name":"University of Toronto","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003579","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100013873","name":"Government of Ontario","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100013873","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Olsen Fund"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>C19-Diterpenoid alkaloids (C19 DTAs) represent a large family of structurally and biologically complex natural products. Within this class, C6-oxidized natural products have remained largely unsynthesized. Herein, we report an expedient synthesis of the fully functionalized AF-ring fragment of chasmanine. Key to our approach was the use of a Piancatelli rearrangement to access the F ring, which then enabled a Mg alkoxide-templated [4+2] cycloaddition to form the AF-ring fragment. We also report a bench-stable oxidative nitrilation reagent for the conversion of aldehydes into nitriles.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03386","type":"journal-article","created":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T07:04:43Z","timestamp":1790060683000},"page":"12287-12292","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of\na Fully Functionalized Chasmanine AF-Ring\nFragment"],"prefix":"10.1021","volume":"28","author":[{"given":"Colton E.","family":"Johnson","sequence":"first","affiliation":[{"name":"University of Toronto , , , ,","place":["Toronto, ON, Canada, M5S3H6"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4165-3695","authenticated-orcid":true,"given":"Mrinmay","family":"Baidya","sequence":"additional","affiliation":[{"name":"University of Toronto , , , ,","place":["Toronto, ON, Canada, M5S3H6"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0179-2914","authenticated-orcid":true,"given":"Mark","family":"Lautens","sequence":"additional","affiliation":[{"name":"University of Toronto , , , ,","place":["Toronto, ON, Canada, M5S3H6"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,22]]},"reference":[{"issue":"21","key":"2026100208370057500_cit1","doi-asserted-by":"publisher","first-page":"3915","DOI":"10.1055\/s-0037-1611897","article-title":"Recent Advances\nTowards Syntheses of Diterpenoid Alkaloids","volume":"51","author":"Dank","year":"2019","journal-title":"Synthesis"},{"key":"2026100208370057500_cit2a","first-page":"1","article-title":"The C19-Diterpenoid Alkaloids","volume-title":"The Alkaloids:\nChemistry and Biology","author":"Wang","year":"2010"},{"key":"2026100208370057500_cit2b","first-page":"1","article-title":"Chapter One - The diterpenoid alkaloids","volume-title":"The Alkaloids: Chemistry and Biology","author":"Liu","year":"2022"},{"issue":"1","key":"2026100208370057500_cit2c","doi-asserted-by":"publisher","first-page":"55","DOI":"10.1021\/np50049a009","article-title":"Diterpenoid Alkaloids from Aconitum crassicaule","volume":"50","author":"Wang","year":"1987","journal-title":"J. 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Pharmacol."},{"issue":"3","key":"2026100208370057500_cit3d","doi-asserted-by":"publisher","first-page":"460","DOI":"10.1039\/D1NP00029B","article-title":"Norditerpenoid\nalkaloids from Aconitum and Delphinium: structural relevance in medicine,\ntoxicology, and metabolism","volume":"39","author":"Qasem","year":"2022","journal-title":"Nat. Prod. Rep."},{"issue":"15","key":"2026100208370057500_cit4a","doi-asserted-by":"publisher","first-page":"4990","DOI":"10.1021\/ja00822a048","article-title":"Total synthesis\nof talatisamine, a delphinine type\nalkaloid","volume":"96","author":"Wiesner","year":"1974","journal-title":"J. Am. Chem. Soc."},{"issue":"1\u20132","key":"2026100208370057500_cit4b","doi-asserted-by":"publisher","first-page":"93","DOI":"10.1351\/pac197541010093","article-title":"The total synthesis of racemic talatisamine","volume":"41","author":"Wiesner","year":"1975","journal-title":"Pure Appl. 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Ital."},{"issue":"3","key":"2026100208370057500_cit14a","doi-asserted-by":"publisher","first-page":"813","DOI":"10.1021\/ja00237a029","article-title":"Stereospecific cross-coupling\nof vinyl halides with vinyl tin reagents catalyzed by palladium","volume":"109","author":"Stille","year":"1987","journal-title":"J. Am. Chem. Soc."},{"issue":"25","key":"2026100208370057500_cit14b","doi-asserted-by":"publisher","first-page":"9585","DOI":"10.1021\/ja00025a025","article-title":"Large rate accelerations in the stille\nreaction with tri-2-furylphosphine and triphenylarsine as palladium\nligands: mechanistic and synthetic implications","volume":"113","author":"Farina","year":"1991","journal-title":"J. Am. Chem. Soc."},{"issue":"38","key":"2026100208370057500_cit15a","doi-asserted-by":"publisher","first-page":"15593","DOI":"10.1021\/jacs.1c08615","article-title":"Complex Polyheterocycles and the Stereochemical Reassignment\nof Pileamartine A via Aza-Heck Triggered Aryl C\u2013H Functionalization\nCascades","volume":"143","author":"Jones","year":"2021","journal-title":"J. Am. Chem. Soc."},{"issue":"19","key":"2026100208370057500_cit15b","doi-asserted-by":"publisher","first-page":"6487","DOI":"10.1021\/ja00227a032","article-title":"A mechanistic\nstudy of the Mitsunobu esterification reaction","volume":"110","author":"Hughes","year":"1988","journal-title":"J. Am. Chem. 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