{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,17]],"date-time":"2026-02-17T21:55:10Z","timestamp":1771365310647,"version":"3.50.1"},"reference-count":18,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2021,9,28]],"date-time":"2021-09-28T00:00:00Z","timestamp":1632787200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004396","name":"Thailand Research Fund","doi-asserted-by":"publisher","award":["RSA6180040"],"award-info":[{"award-number":["RSA6180040"]}],"id":[{"id":"10.13039\/501100004396","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004396","name":"Thailand Research Fund","doi-asserted-by":"publisher","award":["DBG6080007"],"award-info":[{"award-number":["DBG6080007"]}],"id":[{"id":"10.13039\/501100004396","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004704","name":"National Research Council of Thailand","doi-asserted-by":"publisher","award":["2562-11892"],"award-info":[{"award-number":["2562-11892"]}],"id":[{"id":"10.13039\/501100004704","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Benzoquinolizidinone systems were synthesized in both enantiomeric forms from L-glutamic acid. The key chiral arylethylglutarimide intermediate was synthesized from dibenzylamino-glutamate and homoveratrylamine. Aldol reaction of the glutarimide afforded a mixture of syn and anti-aldol adducts. Subsequent regioselective hydride reduction of the glutarimide carbonyl followed by N-acyliminium ion cyclization afforded a product with opposite absolute configurations at C3 and C11b. Cope elimination of the dibenzylamino group then converted the two diastereomers into enantiomers.<\/jats:p>","DOI":"10.3390\/molecules26195866","type":"journal-article","created":{"date-parts":[[2021,9,28]],"date-time":"2021-09-28T21:38:09Z","timestamp":1632865089000},"page":"5866","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Enantiodivergent Synthesis of Benzoquinolizidinones from L-Glutamic Acid"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9856-9331","authenticated-orcid":false,"given":"Punlop","family":"Kuntiyong","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Silpakorn University, Muang Nakhon Pathom 73000, Thailand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Duangkamon","family":"Namborisut","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Silpakorn University, Muang Nakhon Pathom 73000, Thailand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kunita","family":"Phakdeeyothin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Silpakorn University, Muang Nakhon Pathom 73000, Thailand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rungrawin","family":"Chatpreecha","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Silpakorn University, Muang Nakhon Pathom 73000, Thailand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kittisak","family":"Thammapichai","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Silpakorn University, Muang Nakhon Pathom 73000, Thailand"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,28]]},"reference":[{"key":"ref_1","unstructured":"Cordell, G.A. 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