- Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes
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Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.
- Elbert, Bryony L.,Lim, Diane S. W.,Gudmundsson, Haraldur G.,O'Hanlon, Jack A.,Anderson, Edward A.
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p. 8594 - 8598
(2014/07/21)
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- Iterative iodocyclization: Total synthesis of polyrhacitide B
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A highly stereoselective total synthesis of polyrhacitide B is reported. Key reactions are an iodocyclization protocol developed in our group, the Maruoka asymmetric allylation, the Bartlett-Smith iodocarbonate cyclization, and iodolactonization.
- Mohapatra, Debendra K.,Krishnarao, P. Sivarama,Bhimireddy, Eswar,Yadav, Jhillu S.
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p. 1639 - 1647
(2014/06/23)
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- Rugulactone derivatives act as inhibitors of NF-κB activation and modulates the transcription of NF-κB dependent genes in MDA-MB-231cells
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Rugulactone and its analogues were synthesized following Horners-Wadsworth-Emmons and ring-closing metathesis as the key reactions. A library of new rugulactone analogues were designed, synthesized and evaluated for their anticancer activity in breast can
- Mohapatra, Debendra K.,Reddy, D. Sai,Janaki Ramaiah,Ghosh, Sowjanya,Pothula, Vikram,Lunavath, Swetha,Thomas, Shine,Pushpa Valli,Bhadra, Manika Pal,Yadav, Jhillu S.
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p. 1389 - 1396
(2014/03/21)
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- Total synthesis and revision of the absolute configuration of seimatopolide B
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The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxyl
- Reddy, Chada Raji,Dilipkumar, Uredi,Reddy, Motatipally Damoder,Rao, Nagavaram Narsimha
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p. 3355 - 3364
(2013/06/05)
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- Oxidative heck vinylation for the synthesis of complex dienes and polyenes
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We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity f
- Delcamp, Jared H.,Gormisky, Paul E.,White, M. Christina
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p. 8460 - 8463
(2013/07/19)
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- Total synthesis of umuravumbolide and hyptolide through silicon-tethered ring-closing metathesis
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The total synthesis of umuravumbolide and hyptolide has been achieved in a efficient manner by using temporary silicon-tethered ring-closing metathesis and cross-coupling reactions as key steps. The stereogenic centres were generated by means of proline-catalysed α-aminoxylation of aldehydes and Brown's asymmetric allylation method. An efficient total synthesis of umuravumbolide and hyptolide has been achieved by using temporary silicon-tethered ring-closing metathesis. The stereogenic centres were generated by using asymmetric allyl boration and proline-catalysed α-aminoxylation with high degrees of enantioselectivity. Copyright
- Chowdhury, Partha Sarathi,Kumar, Pradeep
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p. 4586 - 4593
(2013/07/26)
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- Highly concise and stereoselective total synthesis of (5R,7S)-kurzilactone
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A highly concise and stereoselective total synthesis of (5R,7S)-kurzilactone (1) was performed by a convergent approach by means of a Jacobsen's hydrolytic kinetic resolution, a Horner-Wadsworth-Emmons reaction for the construction of the α,β-unsaturated
- Mohapatra, Debendra K.,Karthik, Pulluri,Yadav, Jhillu S.
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body text
p. 1226 - 1230
(2012/09/22)
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- C(21)-C(40) of tetrafibricin via metal catalysis: Beyond stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles
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Chemical equations presented. The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer
- Kumpulainen, Esa T. T.,Kang, Byungsoo,Krische, Michael J.
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p. 2484 - 2487
(2011/07/09)
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- Iodo-cyclizations: Novel strategy for the total syntheses of polyrhacitide a and epi-cryptocaryolone
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Highly stereoselective total syntheses of polyrhacitide A and epi-cryptocaryolone have been achieved in 11 steps with high overall yield of 24% and 28%, respectively, following a recently developed strategy for the construction of trans-2,6-disubstituted-
- Mohapatra, Debendra K.,Bhimireddy, Eswar,Krishnarao, P. Sivarama,Das, Pragna P.,Yadav
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supporting information; experimental part
p. 744 - 747
(2011/05/05)
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- Fluorous mixture synthesis of four stereoisomers of the C21-C40 fragment of tetrafibricin
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Four stereoisomers of the C21-C40 fragment are synthesized in a single exercise with the aid of fluorous tagging to encode configurations at C37 and C33. After demixing and detagging, the isomers were found to have substantially identical 1H NM
- Zhang, Kai,Curran, Dennis P.
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supporting information; experimental part
p. 667 - 671
(2010/12/18)
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- Stereoselective synthesis of a monocyclic peloruside A analogue
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Chemical Equation Presentation The stereoselective synthesis of the monocyclic peloruside A analogue 4 has been achieved, following a new efficient approach for the introduction of the side chain, involving a late-stage addition of vinyl lithium species 7a to aldehyde 8. Further key steps are a highly diastereoselective allyltitanation reaction and a RCM-based macrocyclization.
- Wulischleger, Christoph W.,Gertsch, Juerg,Altmann, Karl-Heinz
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supporting information; experimental part
p. 1120 - 1123
(2010/06/13)
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- Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive
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The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active.
- Mori, Kenji,Shikichi, Yasumasa,Shankar, Shruti,Yew, Joanne Y.
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experimental part
p. 7161 - 7168
(2010/10/01)
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- Synthesis of (-)-galantinic acid via iterative hydrolytic kinetic resolution and tethered aminohydroxylation
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A new synthetic strategy for (-)-galantinic acid is reported using iterative hydrolytic kinetic resolution and tethered aminohydroxylation as the key steps.
- Dubey, Abhishek,Kauloorkar, Shruti V.,Kumar, Pradeep
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experimental part
p. 3159 - 3164
(2010/06/11)
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- First total syntheses and absolute configuration of rugulactone and 6(R)-(4′-oxopent-2′-enyl)-5,6-dihydro-2H-pyran-2-one
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The first efficient total syntheses of rugulactone and 6(R)-(4′-oxopent-2′-enyl)-5,6-dihydro-2H-pyran-2-one have been achieved in six steps with 51% and 48% overall yield, respectively. The key steps are Jacobsen's hydrolytic kinetic resolution (HKR), Hor
- Mohapatra, Debendra K.,Das, Pragna P.,Sai Reddy,Yadav
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body text
p. 5941 - 5944
(2010/01/18)
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- Synthesis of the C6-C21 segment of amphidinolide E
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(Chemical Equation Presented) A convergent approach to a C6-C21 segment of the polyketide amphidinolide E has been developed through combination of three subunits by allenylindium bromide-aldehyde addition and Suzuki sp 2-sp3 couplin
- Marshall, James A.,Schaaf, Gregory,Nolting, Andrew
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p. 5331 - 5333
(2007/10/03)
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- Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins
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A convergent synthesis of (3R, 5Z, 8E, 10R)-3-hydroxy-8,10-dimethyl-11-phenylundec-5,8-dienoic acid 4, a putative hexaketide intermediate in the biosynthesis of the squalestatins, is described. A key step in the assembly of the carbon framework is the coupling of alkyne 19 with allylic bromide 13 giving, after further functional group manipulations, the target compound as a single diastereomer. The approach may be adapted for the preparation of the corresponding (3S, 5Z, 8E, 10R)-isomer as well as for the incorporation of carbon-13 labels required for biosynthetic studies.
- Simpson, Thomas J.,Smith, Robert W.,Westaway, Susan M.,Willis, Christine L.,Buss, Antony D.,Cannell, Richard J. P.,Dawson, Michael J.,Rudd, Brian A. M.
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p. 5367 - 5370
(2007/10/03)
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