{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T15:00:09Z","timestamp":1761490809105},"reference-count":24,"publisher":"Informa UK Limited","issue":"9","license":[{"start":{"date-parts":[[2019,9,2]],"date-time":"2019-09-02T00:00:00Z","timestamp":1567382400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"content-domain":{"domain":["www.tandfonline.com"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[2019,9,2]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n               <jats:p>A concise, unified total synthesis of the two prenylated aromatic polyketides amorfrutins A and C, which exhibit various medicinally important biological profiles such as antimicrobial, PPAR\u03b3 modulating and quorum sensing inhibitory activities, has been achieved from commercially available 3,5-dimethoxybenzaldehyde in 38% and 10% overall yields through nine and ten steps, respectively. The key transformation for the synthesis of amorfrutin A was the Claisen rearrangement of a mono-O-(1,1-dimethylallyl)resorcinol derivative to install the C3-prenyl substituent, while that for the synthesis of amorfrutin C was the double Claisen rearrangement of a di-O-(1,1-dimethylallyl)resorcinol derivative to introduce the two prenyl groups at the C3 and C5 positions all at once.<\/jats:p>","DOI":"10.1080\/09168451.2019.1618699","type":"journal-article","created":{"date-parts":[[2019,5,25]],"date-time":"2019-05-25T12:49:55Z","timestamp":1558788595000},"page":"1635-1641","update-policy":"http:\/\/dx.doi.org\/10.1080\/tandf_crossmark_01","source":"Crossref","is-referenced-by-count":9,"title":["Unified total synthesis of amorfrutins A and C via the Claisen rearrangement"],"prefix":"10.1080","volume":"83","author":[{"given":"Tadafumi","family":"Fujita","sequence":"first","affiliation":[{"name":"Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shigefumi","family":"Kuwahara","sequence":"additional","affiliation":[{"name":"Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yusuke","family":"Ogura","sequence":"additional","affiliation":[{"name":"Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"301","published-online":{"date-parts":[[2019,9,2]]},"reference":[{"key":"2021033109482611300_CIT0001","doi-asserted-by":"crossref","first-page":"781","DOI":"10.1016\/0031-9422(81)85174-6","article-title":"Amorfrutin A and B, bibenzyl antimicrobial agents from Amorpha fruticosa","volume":"20","author":"Mitsher","year":"1981","journal-title":"Phytochemistry"},{"key":"2021033109482611300_CIT0002","doi-asserted-by":"crossref","first-page":"1959","DOI":"10.1016\/0031-9422(81)84044-7","article-title":"Isoprenylated resorcinol derivatives from Glycyrrhiza acanthocarpa","volume":"20","author":"Ghisalberti","year":"1981","journal-title":"Phytochemistry"},{"key":"2021033109482611300_CIT0003","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1002\/cbic.201402124","article-title":"Amorfrutins: a promising class of natural products that are beneficial to health","volume":"15","author":"Sauer","year":"2014","journal-title":"Chembiochem"},{"key":"2021033109482611300_CIT0004","doi-asserted-by":"crossref","first-page":"1357","DOI":"10.1039\/C6NP00074F","article-title":"Phytocannabionids: a unified critical inventory","volume":"33","author":"Hanu\u0161","year":"2016","journal-title":"Nat Prod Rep"},{"key":"2021033109482611300_CIT0005","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1021\/acs.jnatprod.5b00072","article-title":"Amorfrutin C induces apoptosis and inhibits proliferation in colon cancer cells through targeting mitochondria","volume":"79","author":"Weidner","year":"2016","journal-title":"J Nat Prod"},{"key":"2021033109482611300_CIT0006","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1021\/acs.jnatprod.6b00809","article-title":"Antibacterial and cytotoxic phenolic metabolites from the fruits of Amorpha fruticosa","volume":"80","author":"Muharini","year":"2017","journal-title":"J Nat Prod"},{"key":"2021033109482611300_CIT0007","doi-asserted-by":"crossref","first-page":"1696","DOI":"10.1021\/np800383q","article-title":"Phenolic constituents of Amorpha fruticosa that inhibit NF-\u03baB activation and related gene expression","volume":"71","author":"Dat","year":"2008","journal-title":"J Nat Prod"},{"key":"2021033109482611300_CIT0008","doi-asserted-by":"crossref","first-page":"7257","DOI":"10.1073\/pnas.1116971109","article-title":"Amorfrutins are potent antidiabetic dietary natural products","volume":"109","author":"Weidner","year":"2012","journal-title":"Proc Natl Acad Sci USA"},{"key":"2021033109482611300_CIT0009","doi-asserted-by":"crossref","first-page":"1802","DOI":"10.1007\/s00125-013-2920-2","article-title":"Amorfrutin B is an efficient natural peroxisome proliferator-activated receptor gamma (PPAR\u03b3) agonist with potent glucose-lowering properties","volume":"56","author":"Weidner","year":"2013","journal-title":"Diabetologia"},{"key":"2021033109482611300_CIT0010","doi-asserted-by":"crossref","first-page":"1160","DOI":"10.1021\/np500747y","article-title":"Amorfrutins are natural PPAR\u03b3 agonists with potent anti-inflammatory properties","volume":"78","author":"Fuhr","year":"2015","journal-title":"J Nat Prod"},{"key":"2021033109482611300_CIT0011","doi-asserted-by":"crossref","first-page":"10268","DOI":"10.1021\/acs.jmedchem.6b01301","article-title":"Design and synthesis of cajanine analogues against hepatitis C virus through down-regulating host chondroitin sulphate N-acetylgalactosaminyltransferase 1","volume":"59","author":"Ji","year":"2016","journal-title":"J Med Chem"},{"key":"2021033109482611300_CIT0012","doi-asserted-by":"crossref","first-page":"2621","DOI":"10.1021\/acs.jnatprod.8b00315","article-title":"Synthesis and biological evaluation of cajaninstillbene acid and amorfrutins A and B as inhibitors of the Pseudomonas aeruginosa quorum sensing system","volume":"81","author":"Xu","year":"2018","journal-title":"J Nat Prod"},{"key":"2021033109482611300_CIT0013","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/j.tetlet.2011.11.019","article-title":"Total synthesis of amorfrutin A via a palladium-catalyzed migratory prenylation-aromatization sequence","volume":"53","author":"Laclef","year":"2012","journal-title":"Tetrahedron Lett"},{"key":"2021033109482611300_CIT0014","doi-asserted-by":"crossref","first-page":"2658","DOI":"10.1016\/j.tetlet.2013.03.042","article-title":"A facile total synthesis of amorfrutin A","volume":"54","author":"Song","year":"2013","journal-title":"Tetrahedron Lett"},{"key":"2021033109482611300_CIT0015","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1021\/ol503135u","article-title":"A common building block for the syntheses of amorfrutin and cajaninstilbene acid libraries toward efficient binding with peroxisome proliferator-activated receptors","volume":"17","author":"Aidhen","year":"2015","journal-title":"Org Lett"},{"key":"2021033109482611300_CIT0016","doi-asserted-by":"crossref","first-page":"12327","DOI":"10.1021\/acs.joc.8b02116","article-title":"Directed C-H bond functionalization: a unified approach to formal syntheses of amorfrutin A, cajaninstilbene acid, hydrangenol, and macrophyllol","volume":"83","author":"Grandhi","year":"2018","journal-title":"J Org Chem"},{"key":"2021033109482611300_CIT0017","unstructured":"Sauer \u00a0S, Weidner \u00a0C, Kliem \u00a0M, et al. Amorfrutin analogs as ppargamma-modulators. US Patent 2014177593, 2014."},{"key":"2021033109482611300_CIT0018","doi-asserted-by":"crossref","DOI":"10.1002\/ejoc.201701811","article-title":"First total synthesis of amorfrutin C and pseudo-amorfrutin A","author":"Miao","year":"2018","journal-title":"Eur J Org Chem"},{"key":"2021033109482611300_CIT0019","doi-asserted-by":"crossref","first-page":"11143","DOI":"10.1021\/ja00103a034","article-title":"Stereoselective total syntheses of amauromine and 5-N-acetylardeemin. A concise route to the family of \u201creverse-prenylated\u201d hexahydropyrroloindole alkaloids","volume":"116","author":"Marsden","year":"1994","journal-title":"J Am Chem Soc"},{"key":"2021033109482611300_CIT0020","article-title":"Synthetic applications of phosphoryl-stabillized anions","author":"Wadsworth","year":"1977","journal-title":"Org React"},{"key":"2021033109482611300_CIT0021","doi-asserted-by":"crossref","first-page":"2001","DOI":"10.1021\/acs.jnatprod.7b00129","article-title":"Prevention of marin biofouling using the natural allelopathic compound batatasin-III and synthetic analogues","volume":"80","author":"Moodie","year":"2017","journal-title":"J Nat Prod"},{"key":"2021033109482611300_CIT0022","doi-asserted-by":"crossref","first-page":"590","DOI":"10.3184\/030823407X256091","article-title":"An efficient synthesis of bibenzylic oxygen heterocycles","author":"Kumbhar","year":"2007","journal-title":"J Chem Res"},{"key":"2021033109482611300_CIT0023","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1071\/CH9881789","article-title":"New depsides from Dimelaena lichens","volume":"41","author":"Elix","year":"1988","journal-title":"Aust J Chem"},{"key":"2021033109482611300_CIT0024","doi-asserted-by":"crossref","first-page":"4886","DOI":"10.1039\/b913496d","article-title":"Evaluation of the pharmacophoric motif of the caged Garcinia xanthones","volume":"7","author":"Chantarasriwong","year":"2009","journal-title":"Org Biomol Chem"}],"container-title":["Bioscience, Biotechnology, and Biochemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/academic.oup.com\/bbb\/article-pdf\/83\/9\/1635\/36828116\/bbb1635.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"http:\/\/academic.oup.com\/bbb\/article-pdf\/83\/9\/1635\/36828116\/bbb1635.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,6,7]],"date-time":"2022-06-07T11:42:35Z","timestamp":1654602155000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/bbb\/article\/83\/9\/1635\/5937742"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,9,2]]},"references-count":24,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2019,9,2]]},"published-print":{"date-parts":[[2019,9,2]]}},"URL":"https:\/\/doi.org\/10.1080\/09168451.2019.1618699","relation":{},"ISSN":["0916-8451","1347-6947"],"issn-type":[{"value":"0916-8451","type":"print"},{"value":"1347-6947","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2019,9,2]]},"published":{"date-parts":[[2019,9,2]]},"assertion":[{"value":"The publishing and review policy for this title is described in its Aims & Scope.","order":1,"name":"peerreview_statement","label":"Peer Review Statement"},{"value":"http:\/\/www.tandfonline.com\/action\/journalInformation?show=aimsScope&journalCode=tbbb20","URL":"http:\/\/www.tandfonline.com\/action\/journalInformation?show=aimsScope&journalCode=tbbb20","order":2,"name":"aims_and_scope_url","label":"Aim & Scope"},{"value":"2019-03-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-04-27","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-05-25","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}