An Improved Three Step Synthesis of (-)-3β-Hydroxycarvone from (-)-Carvone

Santos, Reginaldo Bezerra dos; Brocksom, Timothy J.; Zanotto, Paulo R.; Brocksom, Ursula

doi:10.3390/70200129

Cited by 5 publications

(6 citation statements)

References 13 publications

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“…The obtained mixture was separated on a column with SiO 2 (17 g), with a gradient of EtOAc in hexane from 0% to 100% as eluent, to get 0.138 g (0.83 mmol, 37%) of (5 S ,6 R )- 10 ([α] D 24 −56.4 ( c 1.50, CHCl 3 )). The spectral data of (5 S ,6 R )- 10 corresponded to those described in the literature …”

Section: Methodsmentioning

confidence: 55%

“…Synthesis of (5 S ,6 S )- 10 via the intermediate formation of (−)- 12 and (−)- trans - 13 is described in literature . Note that ref suggested a modified version of the method in ref , offering simplified handling and processing and higher yields of the desired products. When we attempted to use it, however, most of its steps turned out to be irreproducible.…”

Section: Resultsmentioning

confidence: 99%

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Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease

et al. 2011

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(1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 possesses potent antiparkinsonian activity in both MPTP and haloperidol animal models. The use of compound 1 resulted in nearly full recovery of the locomotor and exploratory activities and was as effective as the comparator agent (levodopa). All eight stereoisomers of compound 1 have been synthesized and the influence of the absolute configuration on the antiparkinsonian activity of compound 1 was shown.

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Section: Methodsmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease

et al. 2011

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“…Our synthesis began with the conversion of (+)-carvone ( 6 ) to hydroxyl ketone 11 13 via a Rubottom oxidation (Figure 2). The requisite stereoselective reduction of a-hydroxy ketone 11 to anti- diol 12 proved to be nontrivial.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis, Biological Evaluation, and Target Identification of Rare Abies Sesquiterpenoids

Davis

Hoch

et al. 2018

J. Am. Chem. Soc.

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Abiespiroside A (1), beshanzuenone C (2), and beshanzuenone D (3) belong to the Abies sesquiterpenoid family. Beshanzuenones C (2) and D (3) are isolated from the critically endangered Chinese fir tree species Abies beshanzuensis and demonstrated weak inhibiting activity against protein tyrosine phosphatase 1B (PTP1B). We describe herein the first total syntheses of these Abies sesquiterpenoids relying on the sustainable and inexpensive chiral pool molecule (+)-carvone. The syntheses feature a palladium-catalyzed hydrocarbonylative lactonization to install the 6,6-fused bicyclic ring system and a Dreiding-Schmidt reaction to build the oxaspirolactone moiety of these target molecules. Our chemical total syntheses of these Abies sesquiterpenoids have enabled (i) the validation of beshanzuenone C’s weak PTP1B inhibiting potency, (ii) identification of new synthetic analogs with promising and selective protein tyrosine phosphatase SHP2 inhibiting potency, and (iii) preparation of azide-tagged probe molecules for target identification via a chemoproteomic approach. The latter has resulted in the identification and evaluation of DNA polymerase epsilon subunit 3 (POLE3) as one of the novel cellular targets of these Abies sesquiterpenoids and their analogs. More importantly, via POLE3 inactivation by probe molecule 29 and knockdown experiment, we further demonstrated that targeting POLE3 with small molecules may be a novel strategy for chemosensitization to DNA damaging drugs such as etoposide in cancer.

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“…This reaction involves regioselective and stereoselective a-hydroxylation of ketones via a trimethylsilyl enol ether derivative. 6 (E) MCPBA provides an efficient conversion of cyclic acetals to respective hydroxyalkyl esters. This oxidation using MCPBA gives the product in good to excellent yields under moderate reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

“…2 Cl 2 and aqueous buffer (KH 2 PO 4 /NaOH) as an additive base under mild conditions. 3(B) MCPBA is used along with phenyliodine(III) bis(trifluoroacetate) (PIFA) for the synthesis of dienone lactones from phenyl ether derivatives 6. Here MCPBA acts as a co-oxidant which regenerates the hypervalent iodine(III) species after each cycle, thus making the reaction catalytic 4.…”

mentioning

confidence: 99%