Reaction of isosteviol diterpenoid with selenium dioxide

Kovylyaeva, G. I.; Sharipova, R. R.; Strobykina, I. Yu.; Militsina, O. I.; Мусин, Р. З.; Beskrovnyi, D. V.; Gubaidullin, А. Т.; Al’fonsov, V. A.; Катаев, В. Е.

doi:10.1134/s1070363209120184

Cited by 8 publications

(5 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the second one, which aims to functionalize a -CH 2 placed inside the carbon chain, the reaction occurs slowly and is more difficult to process with respect to the above oxidation reaction. In this case excess SeO 2 together with aqueous EtOH has been used [42][43][44].…”

Section: Resultsmentioning

confidence: 99%

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

et al. 2014

View full text Add to dashboard Cite

Abstract:The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C-3, C-8 and C-9, and a  1,6 -double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms.

show abstract

Section: Resultsmentioning

confidence: 99%

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

et al. 2014

View full text Add to dashboard Cite

show abstract

“…4 ) was reported by Mastalerz et al [ 61 ]. Further, (−)-isosteviol and its esters can be converted into the corresponding 1,2-diketones 5a – c via Riley oxidation [ 62 – 66 ]. The linkage of the two building blocks by condensation reaction of the keto with the amino functionalities presents a promising route for the construction of novel (−)-isosteviol-based C 3 -symmetric scaffolds.…”

Section: Resultsmentioning

confidence: 99%

“…Following path A , (−)-isosteviol can be oxidized under Riley conditions ( Table 1 , reaction conditions a : selenium dioxide/xylene) [ 62 – 63 ] to give the corresponding diketone 9 [ 66 ]. Subsequent esterification with 3,5-dinitrobenzylic chloride under basic conditions ( Table 1 , reaction conditions b for R = DNB) [ 67 ] proceeds with a yield of 57% and leads to the formation of 10 with an overall yield of 46%.…”

Section: Resultsmentioning

confidence: 99%

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

Lohoelter¹,

Brutschy²,

Lubczyk³

et al. 2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe readily available ex-chiral-pool building block (−)-isosteviol was combined with the C 3-symmetric platforms hexahydroxytriphenylene and hexaaminotriptycene providing large and rigid molecular architectures. Because of the persistent cavities these scaffolds are very potent supramolecular affinity materials for head space analysis by quartz crystal microbalances. The scaffolds serve in particular as templates for tracing air-borne arenes at low concentration. The affinities of the synthesized materials towards different air-borne arenes were determined by 200 MHz quartz crystal microbalances.

show abstract

“…For the transformation of ring D of isosteviol, derivatives were initially prepared from the acid 2 or the ethyl ester 2 a ((COCl) 2 / DMF,EtOH), which allowed the preparation, via Baeyer Villiger oxidation, lactones 9 and 10 (Figure 2). Likewise, oxidation of ethyl ester 2 a with SeO 2 yielded diketone 11, [12] and treatment with HCHO in the presence of CH 3 CH 2 ONa/CH 3 CH 2 OH yielded diol 12 [13] . Ethyl ester 2 a was reduced with NaBH 4 /MeOH delivering the corresponding C-16 alcohol, which was then acetylated to ester 13, the same treatment was applied to amide 5, yielding alcohol 14.…”

Section: Ring D Modificationmentioning

confidence: 99%

Synthesis, Cytotoxicity, and Leishmanicidal Evaluation of Ent‐beyerene and Ent‐kaurene Derivatives

et al. 2021

View full text Add to dashboard Cite

Cutaneous leishmaniasis (CL) is an infectious disease endemic of tropical and subtropical countries, for which current pharmacologic treatments have serious drawbacks. Therefore, new and improved medical treatments are required. On the other side, natural products have been a valuable source of bioactive molecules, but unlike other products of natural origin, diterpenoids are molecules with only a few studies as antiparasitic drugs. Continuing our work on syntheses of beyerenes, and focusing on obtaining more compounds with antiparasitic activity, we describe in this work the syntheses and activity of several ent-beyerene and ent-kaurene type of compounds against CL, and also their toxicity. Utilizing classical reactions such as Grignard, Mitsunobu, and Williamson, among others, it was possible to modify rings A and D of entbeyerenes, specifically C-19 on ring A, and C-15 and C-16 on ring D. A total of 40 new compounds were obtained, 21 of them being active against Leishmania (Viannia) braziliensis with median effective concentration (EC 50 ) values less than 25.0 μg/ mL and of these with EC 50 values ranging from 1.8 to 7.1 μg/mL and Selectivity Index (SI) varying from 1.1 to 5.1. All compounds showed to be highly cytotoxic at concentrations less than 100 μg/mL, except compound 37 that was cytotoxic at 279.7 μg/mL and moderately active against L. braziliensis (EC 50 = 33.5 μg/mL and an SI of 8.4. All active compounds were entbeyerene type.

show abstract

Reaction of isosteviol diterpenoid with selenium dioxide

Cited by 8 publications

References 10 publications

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

Synthesis, Cytotoxicity, and Leishmanicidal Evaluation of Ent‐beyerene and Ent‐kaurene Derivatives

Contact Info

Product

Resources

About