{"created":"2023-07-27T06:29:58.298710+00:00","id":14796,"links":{},"metadata":{"_buckets":{"deposit":"d3a0d601-b32b-4a62-89be-6f451e986e05"},"_deposit":{"created_by":3,"id":"14796","owners":[3],"pid":{"revision_id":0,"type":"depid","value":"14796"},"status":"published"},"_oai":{"id":"oai:kanazawa-u.repo.nii.ac.jp:00014796","sets":["1132:1133:1135"]},"author_link":["26369","26481","26480","26479"],"item_4_biblio_info_8":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"1991-01-25","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"1","bibliographicPageEnd":"78","bibliographicPageStart":"75","bibliographicVolumeNumber":"39","bibliographic_titles":[{"bibliographic_title":"Chemical & pharmaceutical bulletin "}]}]},"item_4_description_21":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"A full account is given of the first racemic and chiral syntheses of 11-methoxydihydrocorynantheol [(-)-1], a candidate structure for the Neisosperma alkaloid ochromianine. Coupling of (±)-trans-6-ethoxy-3-ethyl-2,3,4,5-tetrahydro-4-pyridineacetic acid ethyl ester [(±)-6] with 2-chloro-1-(6-methoxy-1H-indol-3-yl)ethanone (4) in the presence of KBr produced the lactam ketone (±)-7,which was then converted into the lactam (±)-9 through the oxazolium salt (±)-8. Bischler-Napieralski cyclization of (±)-9 followed by catalytic hydrogenation gave the tetracyclic ester (±)-11. On reduction with LiAlH_4,(±)-11 yielded the racemic target (±)-1. A parallel synthetic route starting from (+)-6 and 4 afforded the chiral target (-)-1 via (+)-7,8,(+)-9,and (-)-11. Identity of synthetic (-)-1 with ochromianine unequivocally established the structure and absolute stereochemistry of this alkaloid.","subitem_description_type":"Abstract"}]},"item_4_publisher_17":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"日本薬学会"}]},"item_4_relation_12":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"10.1248/cpb.39.75","subitem_relation_type_select":"DOI"}}]},"item_4_source_id_11":{"attribute_name":"NCID","attribute_value_mlt":[{"subitem_source_identifier":"AA00602100","subitem_source_identifier_type":"NCID"}]},"item_4_source_id_9":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"0009-2363","subitem_source_identifier_type":"ISSN"}]},"item_4_version_type_25":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Fujii, Tozo"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Ohba, Masashi"}],"nameIdentifiers":[{},{},{}]},{"creatorNames":[{"creatorName":"Tachinami, Takeshi"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Ohashi, Takako"}],"nameIdentifiers":[{}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2017-10-03"}],"displaytype":"detail","filename":"PE-PR-OHBA-M-75.pdf","filesize":[{"value":"815.1 kB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"PE-PR-OHBA-M-75.pdf","url":"https://kanazawa-u.repo.nii.ac.jp/record/14796/files/PE-PR-OHBA-M-75.pdf"},"version_id":"b444165e-e2ea-4527-8530-8f5f642e5034"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana"}]},"item_type_id":"4","owner":"3","path":["1135"],"pubdate":{"attribute_name":"公開日","attribute_value":"2017-10-03"},"publish_date":"2017-10-03","publish_status":"0","recid":"14796","relation_version_is_last":true,"title":["Quinolizidines. XXVIII. Racemic and chiral syntheses of ochromianine, an indoloquinolizidine alkaloid from Neisosperma miana"],"weko_creator_id":"3","weko_shared_id":3},"updated":"2023-07-27T12:28:41.944281+00:00"}