An improved synthesis of 10-isobornylsultone

Lewis, Frank W.; Grayson, David H.

doi:10.1016/j.tetasy.2014.06.016

Cited by 3 publications

(1 citation statement)

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“…The major step in synthesis of sultone is ring-closing reaction which was often complicated by the need to use special and expensive catalysts such as Rh and Pd [8][9][10]. However, the search for a simple and short synthesis of sultones has never been suspended for a moment in recent years [11]. To facilitate the synthesis of this functional group, in present work, we found a new method to synthesize sulfonic acid lactone derivatives and perform their ring-closing reactions.…”

Section: Introductionmentioning

confidence: 95%

New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

Yan

Zhang

et al. 2015

Molecules

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There has been no remarkable progress in the synthesis of sultones in recent years. To facilitate more detailed studies of this functional group, we found a new method to synthesize the sulfonic acid lactone derivatives and finish its ring-closing reaction. A new sultone derivative, (E)-ethyl 4-oxo-6-styryl-3,4-dihydro-1,2-oxathiine-5-carboxylate 2,2-dioxide (S-CA), was synthesized and structurally identified by 1 H-NMR, 13 C-NMR, HMQC and X-ray single crystal diffraction analysis. The new rapid synthesis extended the method of ring-closing reaction of sulfonic acid lactone derivatives. The angiogenesis activities of S-CA were evaluated by the chick chorioallantoic membrane (CAM) model. It could selectively suppress small angiogenesis in CAM, without influencing either middle and large angiogenesis. In addition, anticancer efficacy of S-CA was evaluated in vivo using a murine sarcoma S180 model. Reduction of the tumor weight and tumor HE staining regions demonstrated that S-CA (10 mg/kg, intraperitoneal injection) had potent inhibition effects and a 44.71% inhibitory rate in S180 mice. Moreover, an acute toxicity test showed that the LD50 value of S-CA via intraperitoneal injection was 25.624 mg/kg.

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Section: Introductionmentioning

confidence: 95%

New Synthesis Method for Sultone Derivatives: Synthesis, Crystal Structure and Biological Evaluation of S-CA

Yan

Zhang

et al. 2015

Molecules

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ChemInform Abstract: An Improved Synthesis of 10‐Isobornylsultone.

Lewis¹,

Grayson²

2015

ChemInform

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An Improved Synthesis of 10-Isobornylsultone. -Target compound (VI) is prepared in 81% overall yield via a 3-step sequence comprising esterification, stereoselective reduction, and base-catalyzed intramolecular cyclization. -(LEWIS*, F. W.; GRAYSON, D. H.; Tetrahedron: Asymmetry 25 (2014) 15, 1150-1152, http://dx.doi.org/10.1016/j.tetasy.2014.06.016 ; Cent. Synth. Chem. Biol., Trinity Coll., Univ. Dublin, Dublin 2, Ire.; Eng.) -M. Tismer

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