- Studies toward the total synthesis of Cytospolide E
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In this manuscript, we describe various approaches that we have examined towards the total synthesis of Cytospolide E. We initially attempted the RCM approach employing first and second generation Grubbs and Grubbs-Hoyeda catalysts resulting in the exclus
- Vadhadiya, Paresh M.,Rout, Jeetendra K.,Ramana
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Read Online
- Synthesis and activity of the archazolid western hemisphere
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A convergent and scalable synthesis of the archazolid western hemisphere has been completed. The V-ATPase inhibitory activity of this compound along with a previously prepared eastern domain was then tested using a convenient Arabidopsis-based V-ATPase as
- Tran, Ann B.,Melly, Geoffrey C.,Doucette, Ryan,Ashcraft, Brook,Sebren, Leanne J.,Havko, Nathan,Young, Jeffery C.,O'Neil, Gregory W.
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Read Online
- Direct Entry to 4,10-Didesmethyl (9S)-Dihydroerythronolide A via Catalytic Allene Osmylation
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Desmethyl erythronolides have emerged as macrolide targets that may prove effective against resistant bacteria. A five-step sequence to 4,10-didesmethyl (9S)-dihydroerythronolide A (1) from known cyclic bis[allene] 13 is reported. Key structural and mechanistic aspects of the synthesis are discussed along with catalytic allene osmylation. An improved route to 13 is also described.
- Yu, Libing,Wang, Huan,Akhmedov, Novruz G.,Sowa, Christopher,Liu, Kai,Kim, Hiyun,Williams, Lawrence
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p. 2868 - 2871
(2016/07/06)
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- NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism
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Two types of NHC-Cu complexes catalyze protoborations of terminal allenes to afford valuable 1,1- or trisubstituted vinylboron species with high site selectivity and stereoselectivity. The scope of the method, application to natural product synthesis, and
- Meng, Fanke,Jung, Byunghyuck,Haeffner, Fredrik,Hoveyda, Amir H.
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supporting information
p. 1414 - 1417
(2013/04/23)
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- Substrate-controlled stereoselectivity in the Yamamoto aldol reaction
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The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products. The Royal Society of Chemistry 2012.
- Schl?ger, Nadin,Kirschning, Andreas
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supporting information
p. 7721 - 7729
(2013/04/23)
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- The first stereoselective total synthesis of the Z-isomer of cytospolide e
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A convergent and highly stereoselective total synthesis of the Z-isomer of cytospolide E has been achieved via Evan's aldol reaction, Sharpless kinetic resolution and RCM cyclisation.
- Yadav,Pandurangam,Suman Kumar,Adi Narayana Reddy,Prasad,Reddy, B.V. Subba,Rajendraprasad,Kunwar
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p. 6048 - 6050
(2012/11/07)
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- Synthesis of the macrolactone of migrastatin and analogues with potent cell-migration inhibitory activity
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The synthesis of the macrolactone core of migrastatin 2, its potent anti-metastasis analogue 34, and ester derivatives 35 and 38 are reported. The approach involves the use of a dihydroxylation reaction to establish the desired C-8 stereocenter followed by a metathesis cyclization reaction. The effects of the compounds on the migration and invasion of human breast cancer cells were evaluated by using the wound-healing and the Boyden-chamber cell-migration and cell-invasion assays. The results revealed a high potency of the macrolactones 2 and 34 and the ester analogues 35 and 38, which suggests they have potential as antimetastatic agents. The synthesis of macrolactones 2 and 34 as well as esters 35 and 38 proceeds in good overall yields. Macrolactone 34 and ester 38 are amongst the most active compoundsof the migrastatin family prepared so far and show good promise as anticancer compounds. Copyright
- Dias, Luiz C.,Finelli, Fernanda G.,Conegero, Leila S.,Krogh, Renata,Andricopulo, Adriano D.
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experimental part
p. 6748 - 6759
(2011/03/21)
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- A stereoselective synthesis of the macrolide core of migrastatin
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A concise and efficient synthesis of the macrolide core of migrastatin, an antimetastatic agent, is reported. In this synthetic protocol, the key intermediate (4R,5S,6S)-6-methoxy-5-(4-methoxybenzyloxy)-2,4-dimethylocta-2,7- dien-1-ol is obtained after di
- Das, Parthasarathi,Saibaba, Vobbalareddy,Kumar, Chetlur Kiran,Mahendar, Velisoju
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p. 445 - 451
(2008/09/20)
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- A short approach to trisubstituted γ-butyrolactones
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The dihydroxylation of unsaturated aldol adducts with catalytic OsO 4 and NMO occurs under very mild conditions and with moderate to excellent levels of diastereoselectivity to give trisubstituted γ-butyrolactone derivatives.
- Dias, Luiz C.,De Castro, Ilton B. D.,Steil, Leonardo J.,Augusto, Tatiana
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p. 213 - 216
(2007/10/03)
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- A convergent synthesis of the macrolide core of migrastatin
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We describe an efficient synthesis of the 14-membered macrolide core 2 of migrastatin via key intermediate 3 employing a diastereoselective aldol condensation, Lewis acid mediated diastereoselective addition and an exclusive (Z)-olefination sequence. Yama
- Sai Baba,Das, Parthasarathi,Mukkanti,Iqbal, Javed
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p. 6083 - 6086
(2007/10/03)
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- Ketolide antibacterials
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The present invention includes compounds of the formula wherein: X is hydrogen or halide; R2is hydrogen, acyl, or a hydroxy protecting group; R6is hydrogen, hydroxyl, or —ORawherein Rais a substituted or unsubstituted moiety selected from the group consisting of C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, aryl, heterocyclo, aryl(C1-C10)alkyl, aryl(C2-C10)alkenyl, aryl(C2-C10)alkynyl, heterocyclo(C1-C10)alkyl, heterocyclo(C2-C10)alkenyl, and heterocyclo(C2-C10)alkynyl; R13is hydrogen or a substituted or unsubstituted moiety wherein the moiety is selected from the group consisting of methyl; C3-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, aryl, heterocyclo, aryl(C1-C10)alkyl, aryl(C2-C10)alkenyl, aryl(C2-C10)alkynyl, heterocyclo(C1-C10)alkyl, heterocyclo(C2-C10)alkenyl, and heterocyclo(C2-C10)alkynyl; and, R is hydrogen or a substituted or unsubstituted moiety wherein the moiety is selected from the group consisting of C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, aryl, heterocyclo, aryl(C1-C10)alkyl, aryl(C2-C10)alkenyl, aryl(C2-C10)alkynyl, heterocyclo(C1-C10)alkyl, heterocyclo(C2-C10)alkenyl, and heterocyclo(C2-C10)alkynyl; and the pharmaceutically acceptable salts, esters and pro-drug forms thereof. These compounds possess anti-infective activity and are useful for the treatment of bacterial and protozoal infections.
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- Macrolide antiinfective agents
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The invention is directed towards antibacterial compounds. The invention concerns macrolide antibiotics useful as antiinfective agents.
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- Racemic thioesters for production of polyketides
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Facile methods for preparing diketide and triketide thioesters are disclosed. The resulting thioesters may be used as intermediates in the synthesis of desired polyketides, and may contain functional groups which ultimately reside in side chains on the resulting polyketide and thus can be used further to manipulate the polyketide so as form derivatives. The polyketides produced may also be tailored by glycosylation, hydroxylation and the like. New polyketides and their derivatives and tailored forms are thereby produced.
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- Precursor directed biosynthesis of novel 6-deoxyerythronolide B analogs containing non-natural oxygen substituents and reactive functionalities
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Feeding of synthetic precursors to a blocked mutant of 6- deoxyerythronolide B synthase (DEBS) [1] led to production of novel 6- deoxyerythronolide B analogs in vivo containing additional non-natural oxygen substituents as well as additional reactive groups.
- Hunziker, Daniel,Wu, Nicholas,Kenoshita, Kenji,Cane, David E.,Khosla, Chaitan
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p. 635 - 638
(2007/10/03)
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