Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits

dc.creatorSartori, Suélen Karine
dc.creatorMiranda, Izabel L.
dc.creatorMatos, Davi A. de
dc.creatorKohlhoff, Markus
dc.creatorDiaz, Marisa A. N.
dc.creatorDiaz-Muñoz, Gaspar
dc.date2022-02-10T18:11:58Z
dc.date2022-02-10T18:11:58Z
dc.date2021
dc.date.accessioned2023-09-26T20:42:06Z
dc.date.available2023-09-26T20:42:06Z
dc.identifierSARTORI, Suélen Karine et al. Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits. J. Braz. Chem. Soc., v. 32, n. 4, p. 757- 766, 2021 • https://doi.org/10.21577/0103-5053.20200227
dc.identifier0103-5053
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/51142
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8862291
dc.descriptionThis study describes the stereoselective synthesis of two new γ-lactones in 6 and 3 steps and 19 and 32% yield, respectively, directed toward the total synthesis of the natural product (−)-cleistenolide. The starting material was an enantiomerically pure diacetonide diol, derived from d-mannitol with the required stereocenters for (−)-cleistenolide synthesis. γ-Lactone syntheses were based on highly selective protection and deprotection of hydroxyls from d-mannitol. The formation of γ-lactone rings was the culmination of this approach, made possible by a Horner-Wadsworth-Emmons Z-olefination between diacetal aldehyde and ethyl 2-(bis(o-tolyloxy)phosphoryl)acetate to produce an unsaturated ester. The Z-isomer ester was highly favored in relation to the E-isomer (Z/E ratio of 94:6), allowing the formation of the γ-lactone ring under acid catalysis. This strategy precluded the use of chiral auxiliaries or catalysts for the control of stereocenters in the novel γ-lactones
dc.formatapplication/pdf
dc.languageeng
dc.publisherSociedade Brasileira de Química
dc.rightsopen access
dc.subject(−)-cleistenolide
dc.subjectγ-lactone
dc.subjectdiacetonide diol
dc.subjectd-mannitol
dc.titleSynthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
dc.typeArticle


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