127793-67-3Relevant academic research and scientific papers
Synthesis and glycosidase inhibition of broussonetine M and its analogues
Wu, Qing-Kun,Kinami, Kyoko,Kato, Atsushi,Li, Yi-Xian,Jia, Yue-Mei,Fleet, George W.J.,Yu, Chu-Yi
, (2019)
Cross-metathesis (CM) and Keck asymmetric allylation, which allows access to defined stereochemistry of a remote side chain hydroxyl group, are the key steps in a versatile synthesis of broussonetine M (3) from the D-arabinose-derived cyclic nitrone 14. By a similar strategy, ent-broussonetine M (ent-3) and six other stereoisomers have been synthesized, respectively, starting from L-arabino-nitrone (ent-14), L-lyxo-nitrone (ent-3-epi-14), and L-xylo-nitrone (2-epi-14) in five steps, in 26%–31% overall yield. The natural product broussonetine M (3) and 10’-epi-3 were potent inhibitors of β-glucosidase (IC50 = 6.3 μM and 0.8 μM, respectively) and β-galactosidase (IC50 = 2.3 μM and 0.2 μM, respectively); while their enantiomers, ent-3 and ent-10’-epi-3, were selective and potent inhibitors of rice α-glucosidase (IC50 = 1.2 μM and 1.3 μM, respectively) and rat intestinal maltase (IC50 = 0.29 μM and 18 μM, respectively). Both the configuration of the polyhydroxylated pyrrolidine ring and C-10’ hydroxyl on the alkyl side chain affect the specificity and potency of glycosidase inhibition.
An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline via Keck allylation and CBS reduction
Bhoite, Shubhangi P.,Kamble, Rohit B.,Suryavanshi, Gurunath M.
, p. 4704 - 4705 (2015)
Abstract An enantioselective synthesis of (+)-hygroline and (+)-pseudohygroline has been achieved in high optical purity (98% ee) from readily available 1,4-butanediol. The synthesis strategy employs a Keck allylation, CBS reduction, and Wacker oxidation.
A practical synthesis of C14-C26 fragment of anticancer drug, eribulin mesylate Dedicated to Dr. M. Lakshmi Kantam on her 60th birthday
Lavanya, Nadella,Kiranmai, Nayani,Mainkar, Prathama S.,Chandrasekhar, Srivari
supporting information, p. 4283 - 4285 (2015/06/22)
High yielding synthesis of C14-C26 fragment of eribulin is achieved from commercially available R-(+)-citronellol and 1,4-butane diol utilizing the chirality of citronellol 'methyl' centre as C25, organocatalytic epoxidation to install C23 chirality and Sharpless asymmetric dihydroxylation to install chirality at C20 and C17.
Asymmetric synthesis of the C14-C26 building block of eribulin mesylate
Murthy, Akondi Srirama,Mahipal, Bodugum,Chandrasekhar, Srivari
, p. 6959 - 6966 (2013/02/23)
An alternative route for the synthesis of the C14-C26 building block of the anticancer drug eribulin mesylate is described. The key steps involved in the synthesis are a Julia-Kocienski olefination between aldehyde 4 and sulfone 5 and a tandem Sharpless asymmetric dihydroxylation/SN2 cyclisation reaction on mesyl compound 3. Copyright
A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters
Fuwa, Haruhiko,Mizunuma, Kana,Matsukida, Seiji,Sasaki, Makoto
supporting information; experimental part, p. 4995 - 5010 (2011/08/06)
In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an efficient manner under mild conditions. AgOTf-promoted intramolecular oxa-conjugate cyclization of β-hydroxy ynones provided 2,6-substituted dihydropyrones in excellent yields. On the other hand, acid-catalyzed cyclization of β-hydroxy enones caused racemization of the product 2,6-substituted tetrahydropyrones due to its reversible nature. Eventually, stereoselective hydrogenation of substituted dihydropyrones was found to be a solid and efficient approach for the synthesis of 2,6-cis-substituted tetrahydropyrone derivatives.
Highly demanding cross-metathesis in the synthesis of the C16-C30 fragment of dolabelide C
Braun, Marie-Gabrielle,Vincent, Aurelie,Boumediene, Mehdi,Prunet, Joelle
, p. 4921 - 4929 (2011/08/03)
A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.
SYNTHESIS AND ANTICANCER ACTIVITY OF NEW ACTIN-TARGETING SMALL-MOLECULE AGENTS
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Page/Page column 2; 15, (2010/09/05)
The present invention provides a novel bistramide analog useful for treating various types of cancer.
Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: Departure from chirally modified allyl metal reagents in carbonyl addition
Kim, In Su,Ngai, Ming-Yu,Krische, Michael J.
supporting information; experimental part, p. 14891 - 14899 (2009/02/08)
Under the conditions of transfer hydrogenation employing an iridium catalyst generated in situ from [Ir(COd)Cl]2, chiral phosphine ligand (R)-BINAP or (R)-Cl,MeO-BIPHEP, and m-nitrobenzoic acid, allyl acetate couples to allylic alcohols 1a-c, aliphatic alcohols 1d-1, and benzylic alcohols 1m-u to furnish products of carbonyl allylation 3a-u with exceptional levels of asymmetric induction. The very same set of optically enriched carbonyl allylation products 3a-u are accessible from enals 2a-c, aliphatic aldehydes 2d-1, and aryl aldehydes 2m-u, using iridium catalysts ligated by (-)-TMBTP or (R)-Cl,MeO-BIPHEP under identical conditions, but employing isopropanol as a hydrogen donor. A catalytically active cyclometallated complex V, which arises upon ortho-C-H insertion of iridium onto m-nitrobenzoic acid, was characterized by single-crystal X-ray diffraction. The results of isotopic labeling are consistent with intervention of symmetric iridium π-allyl intermediates or rapid interconversion of σ-allyl haptomers through the agency of a symmetric π-allyl. Competition experiments demonstrate rapid and reversible hydrogenation-dehydrogenation of the carbonyl partner in advance of C-C coupling. However, the coupling products, which are homoallylic alcohols, experience very little erosion of optical purity by way of redox equilibration under the coupling conditions, although isopropanol, a secondary alcohol, may serve as terminal reductant. A plausible catalytic mechanism accounting for these observations is proposed, along with a stereochemical model that accounts for the observed sense of absolute stereoinduction. This protocol for asymmetric carbonyl allylation transcends the barriers imposed by oxidation level and the use of preformed allyl metal reagents.
Enantioselective synthesis of the C1-C15 fragment of dolabelide C
Vincent, Aurélie,Prunet, Jo?lle
, p. 2269 - 2271 (2007/10/03)
A synthesis of the C1-C15 fragment of dolabelide C is reported. The key step is a diastereoselective Mukaiyama aldol reaction to form the C6-C7 bond, followed by reduction and deoxygenation of the carbonyl group at C5. The trisubstituted vinyl iodide is i
Highly enantioselective allylation of aldehydes catalyzed by indium(III) - PYBOX complex
Lu, Jun,Ji, Shun-Jun,Teo, Yong-Chua,Loh, Teck-Peng
, p. 159 - 161 (2007/10/03)
(Chemical Equation Presented) A chiral indium(III) - PYBOX complex prepared from indium triflate and chiral PYBOX has been discovered to effect high enantioselectivities in the addition of allyltributyl stannane to aldehydes. The allylation of a variety of aromatic, α,β-unsaturated, and aliphatic aldehydes resulted in good yields and high enantioselectivities (up to 94% ee).
