Asymmetric synthesis of all the stereoisomers of tarchonanthuslactone

Baktharaman, Sivaraj; Selvakumar, Sermadurai; Singh, Vinod K.

doi:10.1016/j.tetlet.2005.08.164

Cited by 30 publications

(14 citation statements)

References 27 publications

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“…In summary, 1 has no anti-diabetic effect as previously suggested [14,15,16,17,18]. In fact, despite its structural similarities with 2 and 3 , both of which capable of transiently reducing the blood glucose levels of diabetic animals, the accute treatment of diabetic mice with 1 results in a transient increase in blood glucose.…”

Section: Resultsmentioning

confidence: 56%

“…Traditional health practitioners have used T. camphorate for diabetes treatment; moreover, its anti-inflammatory and cytotoxic activities have been reported by van de Venter and coworkers [9]. Tarchonanthuslactone ( 1 ) has a privileged structure, presenting the usually bioactive α,β-unsaturated δ-lactone motif [10,11,12,13], which makes it a good target for new asymmetric synthetic approaches [14,15,16,17,18]. Interestingly, Hsu and coworkers [19] have reported that caffeic acid ( 3 ) has an antidiabetic effect and, because of the structural similarity between 1 and 3 , a number of reports have, thereafter, assigned a putative antidiabetic effect to 1 as well [14,15,16,17,18,20,21,22].…”

Section: Introductionmentioning

confidence: 99%

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(−)-Tarchonanthuslactone Exerts a Blood Glucose-Increasing Effect in Experimental Type 2 Diabetes Mellitus

et al. 2015

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Abstract:A number of studies have proposed an anti-diabetic effect for tarchonanthuslactone based on its structural similarity with caffeic acid, a compound known for its blood glucose-reducing properties. However, the actual effect of tarchonanthuslactone on blood glucose level has never been tested. Here, we report that, in opposition to the common sense, tarchonanthuslactone has a glucose-increasing effect in a mouse model of obesity and type 2 diabetes mellitus. The effect is acute and non-cumulative and is present only in diabetic mice. In lean, glucose-tolerant mice, despite a slight increase in blood glucose levels, the effect was not significant.

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Section: Resultsmentioning

confidence: 56%

Section: Introductionmentioning

confidence: 99%

(−)-Tarchonanthuslactone Exerts a Blood Glucose-Increasing Effect in Experimental Type 2 Diabetes Mellitus

et al. 2015

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“…Later, asymmetric versions of this methodology have been developed by using either chiral substrates or chiral titanium catalysts. For example, Singh et al demonstrated that, under Kulinkovich reaction conditions, chiral b-alkoxy ester 228 afforded the corresponding cyclopropanol 229 as the only detected stereoisomer in high yield (87%), that constituted the key intermediate for the synthesis of all the stereoisomers of tarchonanthuslactone, a naturally occurring biologically active product (Scheme 87) [210].…”

Section: Miscellaneous Asymmetric Cyclopropanations As Key Stepsmentioning

confidence: 99%

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

Dalpozzo¹,

Lattanzi

Pellissier

2017

COC

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This review updates recent applications of asymmetric aziridination, azirination, thiirination, epoxidation, and cyclopropanation in the total synthesis of biologically active compounds, including natural products, using chiral substrates or chiral catalysts, covering the literature since 2000. The interest towards these synthetic methodologies of chiral three-membered rings has increased in the last decade, dictated either by the biological activities that display many naturally occurring products bearing a three-membered unit or by the ring strain of three-membered rings making them useful precursors of many more complex interesting molecules. Classic as well as modern protocols in asymmetric aziridinations, azirinations, epoxidations, thiirinations, and cyclopropanations have been widely applied as key steps of a number of syntheses of important products. Although the use of chiral substrates and auxiliaries is still highly employed particularly in asymmetric aziridination and cyclopropanation, the development of enantioselective catalytic methodologies has witnessed exponential growth during the last decade. The present review is subdivided into three parts, dealing successively with the use of chiral nitrogen-containing three-membered rings, chiral epoxides and thiiranes, and chiral cyclopropanes in total synthesis.

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“…A strong push toward the RCM of allyl butenoates came from the further possibility to isomerize the endocyclic double bond of the pyrone system formed by RCM in the presence of a suitable base (in most cases DBU and KOtBu) or even in the presence of trifluoroacetic acid (Scheme 37) [182][183][184] isomerization allows to effectively turn γ,δ-unsaturated into conjugated valerolactones, thus overcoming all the problems related to the RCM of acrylates. Indeed, in that way it was possible to afford the same conjugated lactones from allyl butenoates as well as from homoallyl acrylates, but using lower loadings in catalysts and higher concentrations in substrates.…”

Section: "Non-acrylate"-type Ring Closurementioning

confidence: 99%