Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4404
DC FieldValueLanguage
dc.contributor.authorA., Crescenzaen_us
dc.contributor.authorBotta, Maurizioen_us
dc.contributor.authorCorelli, Federicoen_us
dc.contributor.authorA., Santinien_us
dc.contributor.authorTafi, Andreaen_us
dc.date.accessioned2021-03-30T14:43:49Z-
dc.date.available2021-03-30T14:43:49Z-
dc.date.issued1999-
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/20.500.12779/4404-
dc.description19463en_US
dc.description.abstractSynthetic routes to highly functionalized 1,4-thiazepinones 2 and 3 have been developed. S-Ac-NBOC-L-Cys-D(L)-ThrOMe 7a,b have been prepared and, after transformation into the corresponding mesylates, used as the cyclization substrates. Treatment of these compounds with LiA1H(OMe)3 in THF results in mesylate elimination and thiolacetate reduction, giving rise to both a Michael acceptor (α,β-unsaturated ester) and Michael donor (thiol anion), which undergo in situ intramolecular conjugate addition leading to the stereoselective formation of only two of the four possible stereoisomers of 2. On the other hand, PCC/CaCO3 oxidation of 7a gave in 80% yield the corresponding ketone 11, which was in turn transformed into the enol triflate 15. Cleavage of the thiolacerate moiety, simultaneous elimination of trifluoromethanesulfonic acid to generate an allene system, and addition of the thiol group to the central carbon of the allene to provide the enantiomerically pure cyclic compound 3 in 85% yield was effected via a one- pot reaction by means of MeONa/MeOH. Thiazepinone 3 is an interesting intermediate for the preparation of conformationally restricted dipeptide mimetics, and its elaboration into the dual ACE/NEP inhibitor 4 is reported.en_US
dc.language.isoenen_US
dc.relationNoneen_US
dc.relation.ispartofJOURNAL OF ORGANIC CHEMISTRYen_US
dc.titleCyclic Dipeptides. 3. Synthesis of Methyl (R)-6-[(tert-Butoxycarbonyl)amino]-4,5,6,7-tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3-carboxylate and Its Hexahydro Analogs. Elaboration of a Novel Dual ACE/NEP Inhibitoren_US
dc.typeArticleen_US
dc.identifier.doi10.1021/jo981425ven_US
dc.identifier.scopus2-s2.0-0033617331en_US
dc.identifier.isiWOS:000080171200017en_US
dc.relation.volume64en_US
dc.relation.issue9en_US
dc.description.firstpage3019en_US
dc.description.lastpage3025en_US
dc.description.thirdmissionNot applicableen_US
item.cerifentitytypePublications-
item.grantfulltextnone-
item.languageiso639-1en-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.openairetypeArticle-
item.fulltextNo Fulltext-
crisitem.author.orcid0000-0003-0456-6995-
crisitem.author.orcid0000-0002-5750-4504-
crisitem.author.orcid0000-0003-4308-3531-
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