{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T01:22:06Z","timestamp":1790212926675,"version":"4.1.0"},"reference-count":34,"publisher":"American Chemical Society (ACS)","issue":"14","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2008,7,17]]},"DOI":"10.1021\/ol801094e","type":"journal-article","created":{"date-parts":[[2008,6,13]],"date-time":"2008-06-13T07:01:05Z","timestamp":1213340465000},"page":"3077-3080","source":"Crossref","is-referenced-by-count":33,"title":["Iterative Cr-Mediated Catalytic Asymmetric Allylation To Synthesize <i>syn\/syn<\/i>- and <i>anti\/anti<\/i>-1,3,5-Triols"],"prefix":"10.1021","volume":"10","author":[{"given":"Zhiyu","family":"Zhang","sequence":"first","affiliation":[{"name":"Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sylvain","family":"Aubry","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshito","family":"Kishi","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2008,6,13]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"3073","DOI":"10.1021\/ol801093p","volume":"10","author":"Zhang Z.","year":"2008","journal-title":"Org. Lett."},{"key":"ref2\/cit2","unstructured":"The 1,3-polyol structure cluster is present in numerous natural products ranging from antibiotics to marine natural products. A substructure search with SciFinder gave 87 and 35 natural products bearing one or more of 1,3,5,7,9-pentaol(s) and 1,3,5,7,9,11,13-heptaol(s), respectively."},{"key":"ref3\/cit3","unstructured":"For example, see:"},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"1181","DOI":"10.1016\/0031-9422(79)80130-2","volume":"18","author":"Mynderse J. S.","year":"1979","journal-title":"Phytochemistry"},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"4431","DOI":"10.1021\/jo00301a041","volume":"55","author":"Carmeli S.","year":"1990","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3c","doi-asserted-by":"crossref","first-page":"11133","DOI":"10.1016\/S0040-4020(01)89416-3","volume":"50","author":"Mori Y.","year":"1994","journal-title":"Tetrahedron"},{"key":"ref3\/cit3d","doi-asserted-by":"crossref","first-page":"6529","DOI":"10.1016\/S0040-4039(01)89013-4","volume":"30","author":"Nakata T.","year":"1989","journal-title":"Tetrahedron Lett."},{"key":"ref3\/cit3e","doi-asserted-by":"crossref","first-page":"1559","DOI":"10.1021\/jo00031a041","volume":"57","author":"Rychnovsky S. D.","year":"1992","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3f","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1021\/np020040b","volume":"65","author":"Rao M. R.","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref4\/cit4","unstructured":"For reviews on this subject, see:"},{"key":"ref4\/cit4a","first-page":"557","author":"Bode S. E.","year":"2006","journal-title":"Synthesis"},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.1002\/(SICI)1521-3773(19980605)37:10<1375::AID-ANIE1375>3.0.CO;2-H","volume":"37","author":"Schneider C.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"2021","DOI":"10.1021\/cr00038a011","volume":"95","author":"Rychnovsky S. D.","year":"1995","journal-title":"Chem. Rev."},{"key":"ref4\/cit4d","doi-asserted-by":"crossref","first-page":"2041","DOI":"10.1021\/cr00038a012","volume":"95","author":"Norcross R. D.","year":"1995","journal-title":"Chem. Rev."},{"key":"ref4\/cit4e","doi-asserted-by":"crossref","first-page":"1307","DOI":"10.1021\/cr00020a002","volume":"93","author":"Hoveyda A. M.","year":"1993","journal-title":"Chem. Rev."},{"key":"ref4\/cit4f","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1055\/s-1990-26966","author":"Oishi T.","year":"1990","journal-title":"Synthesis"},{"key":"ref4\/cit4g","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1002\/anie.198405561","volume":"23","author":"Reetz M. T.","year":"1984","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1021\/ol991349y","volume":"2","author":"BouzBouz S.","year":"2000","journal-title":"Org. Lett."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"3361","DOI":"10.1016\/S0040-4039(00)00451-2","volume":"41","author":"BouzBouz S.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"3975","DOI":"10.1021\/ol0063914","volume":"2","author":"BouzBouz S.","year":"2000","journal-title":"Org. Lett."},{"key":"ref5\/cit5d","doi-asserted-by":"crossref","first-page":"1982","DOI":"10.1021\/jo010653d","volume":"67","author":"Cossy J.","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref5\/cit5e","doi-asserted-by":"crossref","first-page":"1453","DOI":"10.1021\/ol070240k","volume":"9","author":"Amans D.","year":"2007","journal-title":"Org. Lett"},{"key":"ref5\/cit5f","doi-asserted-by":"crossref","first-page":"1864","DOI":"10.1021\/jo701315h","volume":"73","author":"Ferri\u00e9 L.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"2321","DOI":"10.1021\/ja00033a005","volume":"114","author":"Hafner A.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref7\/cit7","unstructured":"For a review on this subject, see:"},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/anie.198500013","volume":"24","author":"Masamune S.","year":"1985","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref8\/cit8","unstructured":"With use of TMS-Cl as the dissociating agent, the transformation of1into2could be achieved in a single step. Under this condition, however, the rate of coupling was significantly slower and the yield was lower."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"12248","DOI":"10.1021\/ja045557j","volume":"126","author":"Kurosu M.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10","unstructured":"Protection with an ether (PMB) or silyl ether (TES and TBS) group made the rate of allylation to be significantly slower. Protection with an acyl (Ac and MeOAc) group gave an excellent result in terms of asymmetric induction, but products were often accompanied with the corresponding elimination by-products. In addition, the rate of allylation with an aldehyde bearing a free alcohol was found to be very slow."},{"key":"ref11\/cit11","unstructured":"The oxidative cleavage could be done in one step (O3, followed by PPh3treatment or OsO4\/NaIO4) or two steps (OsO4\/NMO, followed by NaIO4treatment or by Pb(OAc)4treatment). Among them, the procedure of OsO4\/NMO, followed by Pb(OAc)4treatment, gave the best yield."},{"key":"ref12\/cit12","unstructured":"For details, see theSupporting Information."},{"key":"ref13\/cit13","unstructured":"These transformations were first studied withsyn-3(de = 92%) andanti-3(de = 95%). The diastereomeric purity of resultantsyn\/syn-4andanti\/anti-4was estimated to be de = 93% and 91%, respectively."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"2562","DOI":"10.1002\/1522-2675(20000906)83:9<2562::AID-HLCA2562>3.0.CO;2-Z","volume":"83","author":"Kobayashi Y.","year":"2000","journal-title":"Helv. Chim. Acta"},{"key":"ref15\/cit15","unstructured":"In DMSO-d6,anti\/anti-anti\/syn- andsyn\/syn-1,3,5-triols give the characteristic chemical shift at 63.9 \u00b1 0.5 ppm, 66.2 \u00b1 0.5 ppm, and 68.2 \u00b1 0.5 ppm, respectively."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol801094e","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,6]],"date-time":"2023-03-06T17:03:43Z","timestamp":1678122223000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol801094e"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,6,13]]},"references-count":34,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2008,7,17]]}},"alternative-id":["10.1021\/ol801094e"],"URL":"https:\/\/doi.org\/10.1021\/ol801094e","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,6,13]]}}}