- A new and short method for the synthesis of 2,4-methanoproline
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2,4-Methanoproline, a supposed non-proteinogenic anti-feedant, was synthesised in 5 steps starting from allyl benzyl ether 3 in 10% overall yield with an intramolecular nucleophilic substitution as the key step for the formation of the bicyclic skeleton.
- Rammeloo, Thomas,Stevens, Christian V.
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Read Online
- An efficient route to 3-substituted cyclobutanone derivatives
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An efficient route to 3-(hydroxymethyl)cyclobutanone acetals via a [2+2] cycloaddition reaction is reported. The dramatic effect of different diol acetals on benzyl deprotection is discussed. Efficient synthesis of two synthetically useful intermediates, 3-methylenecyclobutanone acetal and 3-(bromomethyl)cyclobutanone, are provided.
- Kabalka, George W.,Yao, Min-Liang
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Read Online
- Direct syntheses of spiro- and fused-hydrofurans by a tunable tandem semipinacol rearrangement/oxa-michael addition protocol
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A highly chemoselective one-pot reaction has been developed involving a tandem semipinacol rearrangement/oxa-Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro- or fused-dihydrofuran products (see scheme). This one-pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives. Copyright
- Li, Bao-Sheng,Liu, Wen-Xing,Zhang, Qing-Wei,Wang, Shao-Hua,Zhang, Fu-Min,Zhang, Shu-Yu,Tu, Yong-Qiang,Cao, Xiao-Ping
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supporting information
p. 5246 - 5249
(2013/05/22)
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- BORON COMPOUND WITH AMINO ACID SKELETON CONTAINING CYCLO RING
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The purpose of the present invention is to provide a novel boron-containing compound utilizable in BNCT and so on and a process for preparing same. According to the process, a boron compounds having an amino acid skeleton containing cyclo-type rings or a
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Paragraph 0054; 0055
(2013/06/27)
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- Pre-steady state kinetic analysis of cyclobutyl derivatives of 2′-deoxyadenosine 5′-triphosphate as inhibitors of HIV-1 reverse transcriptase
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Pre-steady state kinetic analysis was utilized for biochemical evaluation of a series of cyclobutyl adenosine nucleotide analogs with HIV-1 RT WT. The phosphonyl-diphosphate form of the cyclobutyl nucleotide, 5, was the most efficiently incorporated of the series. Nucleotide 5 was fourfold more efficiently incorporated than the FDA approved TFV-DP by RTWT. The kinetics of incorporation for 5 using the drug resistant mutant enzyme K65R was also determined. Compound 5 was threefold more efficiently incorporated compared to TFV-DP with RTK65R. These results demonstrate cyclobutyl adenosine analogs can act as substrates for incorporation by HIV-1 RT and be a potential scaffold for HIV inhibitors.
- Kim, Jiae,Wang, Ligong,Li, Yongfeng,Becnel, Kimberlynne D.,Frey, Kathleen M.,Garforth, Scott J.,Prasad, Vinayaka R.,Schinazi, Raymond F.,Liotta, Dennis C.,Anderson, Karen S.
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supporting information; experimental part
p. 4064 - 4067
(2012/07/14)
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- Palladium-catalyzed diastereo- and enantioselective Wagner-Meerwein shift: Control of absolute stereochemistry in the C-C bond migration event
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Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a π-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the π-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an α-chiral O-tertiary center which has various synthetic applications.
- Trost, Barry M.,Xie, Jia
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p. 6231 - 6242
(2008/12/20)
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- Comparing the stereoselective biooxidation of cyclobutanones by recombinant strains expressing bacterial baeyer - Villiger monooxygenases
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Microbial Baeyer - Villiger oxidation of representative prochiral ketones with a cyclobutanone structural motif was investigated using a collection of eight monooxygenases of different bacterial origin. This platform of enzymes is able to perform stereoselective biotransformations on an array of structurally diverse substrates. With several ketone precursors, biooxidations yielded enantiocomplementary butyrolactones as key intermediates for the synthesis of natural products and bioactive compounds. The microbial Baeyer - Villiger oxidation allows a facile and rapid entry to several compound classes in a desymmetrization reaction upon de novo generation of chirality.
- Rudroff, Florian,Rydz, Joanna,Ogink, Freek H.,Fink, Michael,Mihovilovic, Marko D.
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p. 1436 - 1444
(2008/09/17)
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- AZETIDINE DERIVATIVES AS GLYT1 INHIBITORS
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The present invention relates to compounds of formula (I); and pharmaceutically acceptable salts thereof and individual enantiomers and diastereomers thereof, as GIyTl inhibitors for treating neurological and psychiatric disorders.
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Page/Page column 26; 54
(2010/11/27)
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- USE OF PDE7 INHIBITORS FOR THE TREATMENT OF NEUROPATHIC PAIN
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The present invention relates to the use of a phosphodiesterase 7 (PDE7) inhibitor in the manufacture of a medicament for the treatment of neuropathic pain and to a method of treating neuropathic pain using an inhibitor of PDE7.
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Page/Page column 77
(2008/06/13)
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- Palladium-catalyzed asymmetric ring expansion of allenylcyclobutanols: An asymmetric Wagner-Meerwein shift
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In this study, we developed a palladium-catalyzed atom economic asymmetric Wagner-Meerwein shift of allenylcyclobutanol substrates. It is an excellent method for creating functionalized cyclopentanones with an α-chiral O-tertiary center by ring expansion
- Trost, Barry M.,Xie, Jia
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p. 6044 - 6045
(2007/10/03)
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- 2' AND 3' - SUBSTITUTED CYCLOBUTYL NUCLEOSIDE ANALOGS FOR THE TREATMENT OF VIRAL INFECTIONS AND ABNORMAL CELLULAR PROLIFERATION
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Provided are cyclobutyl nucleosides and methods for their use in treatment of infections including Retroviridae (including HIV), Hepadnaviridae (including HBV), or Flaviviridae (including BVDV and HCV) infection, or conditions related to abnormal cellular
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Page/Page column 59; 62
(2008/06/13)
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- SOLID-PHASE PREPARATION OF 18F-LABELLED AMINO ACIDS
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A process for the production of an 18F-labelled tracer which comprises treatment of a solid support-bound precursor of formula (I): SOLID SUPPORT-LINKER-SO2-O -TRACER (I) with 18F- to produce the labelled tracer of formula (II).
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- Synthesis of 1-amino-3-[(dihydroxyboryl)methyl]-cyclobutanecarboxylic acid as a potential therapy agent
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A novel boronated aminocyclobutanecarboxylic acid (1) was synthesized for potential use in boron neutron capture therapy. Starting from the readily available 3-(bromomethyl)cyclobutanone ketal (4), several synthetic routes to 1 were evaluated. After sever
- Kabalka, George W.,Yao, Min-Liang
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p. 8280 - 8286
(2007/10/03)
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- Synthesis of 1-[cis-3-(hydroxymethyl)cyclobutyl]-uracil, -thymine and -cytosine
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4-(Benzylsulfanyl)pyrimidin-2(1H)-one 6a is prepared from 1-benzoyluracil 10a in three steps and in satisfactory overall yield. Reproducible conditions are found for the cycloaddition reaction between allyl benzyl ether and dichloroketene, leading to the
- Frieden, Miriam,Giraud, Matthieu,Reese, Colin B.,Song, Quanlai
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p. 2827 - 2832
(2007/10/03)
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- Synthesis of 9--adenine and -guanine
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2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50percent yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in ca. 40percent overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b.The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60percent yield.The former product 22 was converted in three steps and in 39percent overall yield into 9-adenine 6, and the latter product was converted in four steps and in 42percent overall yield into 9-guanine 7.X-Ray crystallographic data relating to compounds 22 and 24 are also reported.
- Kaiwar, Vijay,Reese, Colin B.,Gray, Emily J.,Neidle, Stephen
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p. 2281 - 2288
(2007/10/02)
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