A Straightforward Synthesis of (−)-Phaseolinic Acid

Amador, Marta; Ariza, Xavier; García, Jordi; Ortiz, Joana

doi:10.1021/jo048705x

Cited by 47 publications

(13 citation statements)

References 40 publications

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“…[17] Garcia and co-workers utilized the temporary silicon-tethered ring-closing metathesis as a key strategy in the synthesis of (À)-phaseolinic acid. [18] This natural product belongs to the class of g-butyrolactones that display notable antibacterial, antifungal, and antitumor biological activities. Garcia and co-workers prepared the C 2 -symmetrical 1,4-diol by the standard TST-RCM chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis of (À)-phaseolinic acid 12 was completed through the ozonolysis of pendant alkene followed by NaClO 2 oxidation of the crude aldehyde without the loss of optical purity. [18] The synthesis of unsymmetrical bisA C H T U N G T R E N N U N G (alkoxy)silanes is frequently hampered by the formation of undesired, symmetrical bisA C H T U N G T R E N N U N G (alkoxy)silanes. Usual protocol for the preparation of unsymmetrical bisA C H T U N G T R E N N U N G (alkoxy)silanes includes a silylation of the first alcohol with large excess of dialkyldichlorosilane under dilute conditions.…”

Section: Introductionmentioning

confidence: 99%

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Temporary Silicon‐Tethered Ring‐Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis

Čusak

2012

Chemistry A European J

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Temporary silicon-tethered ring-closing metathesis represents an important cross-coupling strategy for the formation of medium-sized silacycles. These intermediates are valuable synthons in organic synthesis due to their propensity to undergo a facile refunctionalization through protodesilylation, oxidation, silane-group transfer or transmetallation. A particularly attractive utility of this methodology is an application in the synthesis of biologically important natural products. The purpose of this review article is to highlight the recent progress in methodology development and its strategic application toward the target-directed synthesis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Temporary Silicon‐Tethered Ring‐Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis

Čusak

2012

Chemistry A European J

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“…Saponification of 4 with sodium methoxide in methanol provided d-altritol (5) in 88% yield. Ariza et al utilized the TST-RCM in conjunction with the Ireland-Claisen rearrangement to facilitate the total synthesis of (−)-phaseolinic acid (Scheme 8.3) [14]. The C 2 -symmetrical silaketal 6 was prepared in 58% overall yield using an adaptation of the protocol described by Evans and Murthy [13], which employed enantiomerically enriched propargylic alcohols to form the symmetrical bis-alkoxysilane rather than allylic alcohols.…”

Section: -Symmetrical Silaketals and Applicationsmentioning

confidence: 99%

Temporary Silicon–Tethered Ring–Closing Metathesis Reactions in Natural Product Synthesis

Evans

2010

Metathesis in Natural Product Synthesis

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“…Based on our previous experience of the stereoselective synthesis of paraconic acids [15], we also synthesized both enantiomers of UB006 separately to study possible differences in their biological properties ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

(−)-UB006: A new fatty acid synthase inhibitor and cytotoxic agent without anorexic side effects

Makowski

Mir

Mera

et al. 2017

European Journal of Medicinal Chemistry

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C75 is a synthetic anticancer drug that inhibits fatty acid synthase (FAS) and shows a potent anorexigenic side effect. In order to find new cytotoxic compounds that do not impact food intake, we synthesized a new family of C75 derivatives. The most promising anticancer compound among them was UB006 ((4SR,5SR)-4-(hydroxymethyl)-3-methylene-5-octyldihydrofuran-2(3H)-one). The effects of this compound on cytotoxicity, food intake and body weight were studied in UB006 racemic mixture and in both its enantiomers separately. The results showed that both enantiomers inhibit FAS activity and have potent cytotoxic effects in several tumour cell lines, such as the ovarian cell cancer line OVCAR-3. The (-)-UB006 enantiomer's cytotoxic effect on OVCAR-3 was 40-fold higher than that of racemic C75, and 2-and 38-fold higher than that of the racemic mixture and its opposite enantiomer, respectively. This cytotoxic effect on the OVCAR-3 cell line involves mechanisms that reduce mitochondrial respiratory capacity and ATP production, DDIT4/REDD1 upregulation, mTOR activity inhibition, and caspase-3 activation, resulting in apoptosis.In addition, central and peripheral administration of (+)-UB006 or (-)-UB006 into rats and mice did not affect food intake or body weight. Altogether, our data support the discovery of a new potential anticancer compound (-)-UB006 that has no anorexigenic side effects.

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A Straightforward Synthesis of (−)-Phaseolinic Acid

Cited by 47 publications

References 40 publications

Temporary Silicon‐Tethered Ring‐Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis

Temporary Silicon‐Tethered Ring‐Closing Metathesis: Recent Advances in Methodology Development and Natural Product Synthesis

Temporary Silicon–Tethered Ring–Closing Metathesis Reactions in Natural Product Synthesis

(−)-UB006: A new fatty acid synthase inhibitor and cytotoxic agent without anorexic side effects

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