{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,30]],"date-time":"2026-10-30T09:57:20Z","timestamp":1793354240908,"version":"4.5.0"},"reference-count":21,"publisher":"American Chemical Society (ACS)","issue":"43","license":[{"start":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T00:00:00Z","timestamp":1792454400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T00:00:00Z","timestamp":1792454400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T00:00:00Z","timestamp":1792454400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>In this study, novel tricyclic compounds based on bispidine were prepared via a Michael addition\u2013Henry domino reaction. This reaction sequence proceeds under mild conditions with high diastereoselectivity. Postsynthetic transformation pathways for the resulting nitro alcohols were demonstrated, leading to tricyclic amino alcohols of various structures.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01744","type":"journal-article","created":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T17:02:13Z","timestamp":1792515733000},"page":"14341-14345","source":"Crossref","is-referenced-by-count":0,"title":["Conformational Lability of Bispidine as a Route to New Polycyclic Compounds"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8731-6934","authenticated-orcid":true,"given":"Aleksei V.","family":"Medved\u2019ko","sequence":"first","affiliation":[{"name":"Zelinsky Institute of Organic Chemistry RAS , ,","place":["Moscow, Russia, 119991 N.D."]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7884-8579","authenticated-orcid":true,"given":"Sergey Z.","family":"Vatsadze","sequence":"additional","affiliation":[{"name":"Zelinsky Institute of Organic Chemistry RAS , ,","place":["Moscow, Russia, 119991 N.D."]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,20]]},"reference":[{"key":"2026103005075457700_cit1","doi-asserted-by":"publisher","first-page":"59","DOI":"10.1007\/b136348","volume-title":"Chiral Diazaligands for Asymmetric Synthesis","author":"Chuzel","year":"2020"},{"issue":"31","key":"2026103005075457700_cit2","doi-asserted-by":"publisher","first-page":"27862","DOI":"10.1021\/acsomega.3c02179","article-title":"Quinolizidine-Type Alkaloids: Chemodiversity, Occurrence, and Bioactivity","volume":"8","author":"Cely-Veloza","year":"2023","journal-title":"ACS Omega"},{"key":"2026103005075457700_cit3","doi-asserted-by":"publisher","first-page":"273","DOI":"10.1016\/S1460-1567(02)80038-1","volume-title":"Organolithiums: Selectivity for Synthesis","author":"Clayden","year":"2002"},{"key":"2026103005075457700_cit4","doi-asserted-by":"publisher","DOI":"10.1016\/j.gresc.2025.06.005","article-title":"New Avenues for Asymmetric Synthesis: N\u2013H (+)-Sparteine and Analogues","author":"Zeng","year":"2025","journal-title":"Green Synth. Catal."},{"issue":"33","key":"2026103005075457700_cit5","doi-asserted-by":"publisher","first-page":"7575","DOI":"10.1002\/ejoc.201300987","article-title":"5-Substituted Derivatives of the Tricyclic (+)-Sparteine Surrogate in the Enantioselective Lithiation\/Stannylation of an O-Alkyl Carbamate","author":"Breuning","year":"2013","journal-title":"Eur. J. Org. Chem."},{"issue":"35","key":"2026103005075457700_cit6","doi-asserted-by":"publisher","first-page":"12488","DOI":"10.1002\/chem.201502090","article-title":"The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions","volume":"21","author":"Scharnagel","year":"2015","journal-title":"Chem. \u2013 Eur. J."},{"issue":"9","key":"2026103005075457700_cit7","doi-asserted-by":"publisher","first-page":"2432","DOI":"10.1002\/anie.201712852","article-title":"The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular \u201cInside-Out\u201d Approach","volume":"57","author":"Scharnagel","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"issue":"50","key":"2026103005075457700_cit8","doi-asserted-by":"publisher","first-page":"20754","DOI":"10.1021\/acs.inorgchem.3c02340","article-title":"Bispidine Chelators for Radiopharmaceutical Applications with Lanthanide, Actinide, and Main Group Metal Ions","volume":"62","author":"Kopp","year":"2023","journal-title":"Inorg. Chem."},{"issue":"11","key":"2026103005075457700_cit9","doi-asserted-by":"publisher","first-page":"4405","DOI":"10.1039\/D5DT00050E","article-title":"Bispidine Coordination Chemistry","volume":"54","author":"Bleher","year":"2025","journal-title":"Dalt. Trans."},{"issue":"37","key":"2026103005075457700_cit10","doi-asserted-by":"publisher","first-page":"6292","DOI":"10.1039\/c3ob41122b","article-title":"Protonation-Triggered Conformational Modulation of an N,N\u2032-Dialkylbispidine: First Observation of the Elusive Boat\u2013Boat Conformer","volume":"11","author":"Norrehed","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"2026103005075457700_cit11","doi-asserted-by":"publisher","first-page":"103","DOI":"10.1070\/MC1999v009n03ABEH001097","article-title":"First 1H NMR Observation of Chair\u2013Boat Conformers in Bispidinone System. Molecular Structure of 3,7-Diisopropyl-1,5-Diphenyl-3,7-Diazabicyclo-[3.3.1]Nonane-9-One","volume":"9","author":"Vatsadze","year":"1999","journal-title":"Mendeleev Commun."},{"issue":"44","key":"2026103005075457700_cit12","doi-asserted-by":"publisher","first-page":"16476","DOI":"10.1039\/C9DT03480C","article-title":"2,4-Substituted Bispidines as Rigid Hosts for Versatile Applications: From \u03ba-Opioid Receptor to Metal Coordination","volume":"48","author":"Nonat","year":"2019","journal-title":"Dalt. Trans."},{"issue":"62","key":"2026103005075457700_cit13","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301880","article-title":"Structural Variations in Carboxylated Bispidine Ligands: Influence of Positional Isomerism and Rigidity on the Conformation, Stability, Inertness and Relaxivity of Their Mn2+ Complexes","volume":"29","author":"Ndiaye","year":"2023","journal-title":"Chem. \u2013 Eur. J."},{"issue":"11","key":"2026103005075457700_cit14","doi-asserted-by":"publisher","first-page":"7272","DOI":"10.1021\/acs.joc.3c00514","article-title":"Synthesis of N,N\u2032-Unsymmetrical 9-Amino-5,7-Dimethyl-Bispidines","volume":"88","author":"Kalinin","year":"2023","journal-title":"J. Org. Chem."},{"issue":"22","key":"2026103005075457700_cit15","doi-asserted-by":"publisher","first-page":"6241","DOI":"10.1021\/om200824c","article-title":"Synthesis and Coordination Chemistry of N,N -Diallylbispidine","volume":"30","author":"Cui","year":"2011","journal-title":"Organometallics"},{"issue":"35","key":"2026103005075457700_cit16","doi-asserted-by":"publisher","first-page":"9669","DOI":"10.1021\/acs.orglett.5c02839","article-title":"Rotational Motion in Bispidines: A Conformational Study","volume":"27","author":"Migliano","year":"2025","journal-title":"Org. Lett."},{"issue":"3","key":"2026103005075457700_cit17","doi-asserted-by":"publisher","first-page":"610","DOI":"10.1021\/ol3034274","article-title":"Zamamiphidin A, a New Manzamine Related Alkaloid from an Okinawan Marine Sponge Amphimedon Sp","volume":"15","author":"Kubota","year":"2013","journal-title":"Org. Lett."},{"issue":"18","key":"2026103005075457700_cit18","doi-asserted-by":"publisher","first-page":"2831","DOI":"10.1021\/jm00044a002","article-title":"Aza-Tricyclic Substance P Antagonists","volume":"37","author":"Lowe","year":"1994","journal-title":"J. Med. Chem."},{"issue":"21","key":"2026103005075457700_cit19","doi-asserted-by":"publisher","first-page":"5853","DOI":"10.1002\/anie.201701049","article-title":"Formal (4 + 1) Cycloaddition and Enantioselective Michael\u2013Henry Cascade Reactions To Synthesize Spiro[4,5]Decanes and Spirooxindole Polycycles","volume":"56","author":"Huang","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"issue":"17","key":"2026103005075457700_cit20","doi-asserted-by":"publisher","first-page":"2969","DOI":"10.1002\/adsc.202300427","article-title":"Diastereoselective Synthesis of Bicyclo[3.2.1]Octanes via Catalyst-Free Cascade Michael\/Henry Reaction with a Functionalized Vinylogous Nucleophile","volume":"365","author":"An","year":"2023","journal-title":"Adv. Synth. Catal."},{"issue":"12","key":"2026103005075457700_cit21","doi-asserted-by":"publisher","first-page":"2682","DOI":"10.1021\/ol1007795","article-title":"Facile Domino Access to Chiral Bicyclo[3.2.1]Octanes and Discovery of a New Catalytic Activation Mode","volume":"12","author":"Tan","year":"2010","journal-title":"Org. Lett."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01744","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/43\/14341\/68919668\/jo-2026-01744g.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/43\/14341\/68919668\/jo-2026-01744g.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,30]],"date-time":"2026-10-30T09:29:21Z","timestamp":1793352561000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/43\/14341\/5454694\/Conformational-Lability-of-Bispidine-as-a-Route-to"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,20]]},"references-count":21,"journal-issue":{"issue":"43","published-online":{"date-parts":[[2026,10,20]]},"published-print":{"date-parts":[[2026,10,30]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01744","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,20]]}}}