{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T19:25:15Z","timestamp":1790623515225,"version":"4.1.0"},"reference-count":55,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2010,12,10]],"date-time":"2010-12-10T00:00:00Z","timestamp":1291939200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2011,1,3]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The stereoselective total synthesis of the spiroketal containing\n                    <jats:italic>Streptomyces<\/jats:italic>\n                    metabolite (\u2212)\u2010spirofungin A (\n                    <jats:bold>1<\/jats:bold>\n                    ) is described. A key step involved a spiroketalisation controlled by an intramolecular H\u2010bond which favoured the desired spiroketal\n                    <jats:bold>4<\/jats:bold>\n                    (13:1 ratio). The presence of the intramolecular H\u2010bond in\n                    <jats:bold>4<\/jats:bold>\n                    is possibly due to a 1,5\u2010alkyne\u2013oxygen interaction. Other key steps include an efficient cross\u2010metathesis to form the spiroketal precursor, a tin mediated\n                    <jats:italic>syn<\/jats:italic>\n                    \u2010aldol reaction and a Stille cross\u2010coupling reaction to create the C22\uf8ffC23 bond. A final Wittig extension followed by deprotection gave (\u2212)\u2010spirofungin A (\n                    <jats:bold>1<\/jats:bold>\n                    ).\n                  <\/jats:p>","DOI":"10.1002\/chem.201002501","type":"journal-article","created":{"date-parts":[[2010,12,10]],"date-time":"2010-12-10T09:38:16Z","timestamp":1291973896000},"page":"297-304","source":"Crossref","is-referenced-by-count":17,"title":["Stereoselective Total Synthesis of (\u2212)\u2010Spirofungin\u2005A by Utilising Hydrogen\u2010Bond Controlled Spiroketalisation"],"prefix":"10.1002","volume":"17","author":[{"given":"John E.","family":"Lynch","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shannon D.","family":"Zanatta","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan M.","family":"White","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark A.","family":"Rizzacasa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,12,10]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.51.699"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049873e"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1139\/v81-164"},{"key":"e_1_2_6_4_2","unstructured":"For the chemistry and synthesis of spiroketals see:"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00097a015"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272033372969"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050559n"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules13102570"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol052039k"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702440"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702440"},{"key":"e_1_2_6_11_2","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol050589c"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055033z"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol048321t"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0630447"},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)00371-3"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)01184-5"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0491078"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.01.153"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.45.1409"},{"key":"e_1_2_6_22_2","unstructured":"\u00a0"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200200556"},{"key":"e_1_2_6_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200200556"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0214882"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352016"},{"key":"e_1_2_6_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352016"},{"key":"e_1_2_6_26_2","unstructured":"For a similar preference for the single anomeric spiroketal see reference\u2005[8c]."},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1996-5474"},{"key":"e_1_2_6_28_2","unstructured":"\u00a0"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)98454-5"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200301739"},{"key":"e_1_2_6_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200301739"},{"key":"e_1_2_6_31_2","unstructured":"CCDC\u2010794831 (4) and 794832 (15) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo980759h"},{"key":"e_1_2_6_33_2","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39930000572"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29940002481"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/b201038k"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29960001849"},{"key":"e_1_2_6_38_2","unstructured":"For representative examples see:"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00297a037"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00240a022"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)73669-0"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19971092443"},{"key":"e_1_2_6_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199727381"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.05.044"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00362a047"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00293a035"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol702982x"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00025a025"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101961c"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo001646c"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00020a027"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201002501","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201002501","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:37:56Z","timestamp":1760272676000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201002501"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,12,10]]},"references-count":55,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2011,1,3]]}},"alternative-id":["10.1002\/chem.201002501"],"URL":"https:\/\/doi.org\/10.1002\/chem.201002501","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,12,10]]}}}