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Free Radicals
Free Radicals

... Selective oxidation of a primary OH to an aldehyde can be achieved in the presence of a secondary OH: J. Org. Chem., 54, 2970 (1989); Tetrahedron Lett., 31, 2177 (1990). The oxidation can also be performed using NCS under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996), with Iodosobenzene ...
A Convenient Synthesis of Amino Acid Methyl Esters
A Convenient Synthesis of Amino Acid Methyl Esters

... Received: 29 April 2008; in revised form: 5 May 2008 / Accepted: 6 May 2008 / Published: 8 May ...
Free Radical Chemistry and the Preparation of Alkyl
Free Radical Chemistry and the Preparation of Alkyl

... Alkyl bromides, iodides or chlorides can react with Gilman or Grignard reagents in carbon-skeleton building substitution reactions (SN2 mechanism, Ch. 11) Alkyl halides and organic oxidation and reduction (10.9): Formation of Grignard or Gilman reagents can be considered an organic reduction since t ...
Document
Document

... other cases we were unable to isolate the corresponding ester in any detectable amount. Of course, iodosobenzene was quantitively reduced to iodobenzene. A plausible mechanism of this IOB mediated conversion of 1 to 2, outlined in Scheme 2, is analogous to that suggested by Kita et al. for the oxida ...
Document
Document

... • Ethers Cannot Hydrogen Bond w/ one Another • Ethers CAN H-Bond w/ H2O and Alcohols (Soluble in These) Properties of Some Alcohols/Ethers in Tables 11.1 and 11.2 ...
Brominations and Alkene Synthesis CHM 233 Review
Brominations and Alkene Synthesis CHM 233 Review

... Conc. H2SO4/heat ...
CHM 331 : General Organic Chemistry
CHM 331 : General Organic Chemistry

... Conc. H2SO4/heat ...
Chapter 18 – Carbonyl Compounds II (Last Chapter we mostly talk
Chapter 18 – Carbonyl Compounds II (Last Chapter we mostly talk

... nucleophile. This reaction was first discovered in the 1800’s by Hugo Schiff a German Chemist, and the product of this reaction is often referred to as a Schiff base). *** ppt *** Fill in the Reagent of Product in the Box ...
Chemdraw B&W - Pennsylvania State University
Chemdraw B&W - Pennsylvania State University

... yield a dipolar intermediate called a betaine • The intermediate spontaneously decomposes through a four-membered ring to yield alkene and triphenylphosphine oxide, (Ph)3P=O • Formation of the ylide is shown below ...
IN VITRO Research Article  S. NITHIYA *, N. KARTHIK
IN VITRO Research Article  S. NITHIYA *, N. KARTHIK

... of antioxidant evaluation were expressed as mean ± standard error  of  the  mean  (n=3)  and  independent  student’s  t‐test  was  used  to  determine the level of significance (P <0.05).In this study antiradical  activities  of  synthesized  compounds  1­3  and  standard  antioxidant  such  as  asc ...
Ethers and Epoxides
Ethers and Epoxides

... acid–catalyzed dehydration of ethanol – also with other primary alcohols ...
Chapter 18: Ethers and Epoxides
Chapter 18: Ethers and Epoxides

... acid–catalyzed dehydration of ethanol – also with other primary alcohols ...
Organic #2
Organic #2

... Substitution reactions involve swapping one atom in the molecule for another. Butan-2-ol undergoes substitution when reacted with PCl5 /PCl3 / SOCl2 / c. HCl to form 2-chlorobutane, ...
Ethers and Epoxides - faculty at Chemeketa
Ethers and Epoxides - faculty at Chemeketa

... acid–catalyzed dehydration of ethanol – also with other primary alcohols ...
Chapter 11 - Alcohols and Ethers1
Chapter 11 - Alcohols and Ethers1

... retention of conguration in the formation of a sulfonate ester because the C−O bond is not ...
aldehydes and ketones
aldehydes and ketones

OxorheniumCatalyzed Deoxydehydration of Sugars and Sugar
OxorheniumCatalyzed Deoxydehydration of Sugars and Sugar

... precursor,[26] was obtained in 54 % yield in both cases when high temperature and short reaction time were employed. To further diversify the scope of biomass-derived chemicals accessible through DODH, we applied our reaction to inositols, a class of natural carbohydrate.[27] On one hand, one can im ...
Chapter 5
Chapter 5

... functional group High prio group has lowest possible number If not highest priority NH2 is amino and OH is hydroxy substituent General form is n-substit-n-alken-n-yn-n-groupsuffix ...
Green synthesis of 2-amino-7-hydroxy-4-aryl-4H
Green synthesis of 2-amino-7-hydroxy-4-aryl-4H

Catalytic asymmetric carbonyl addition reactions catalysed by group
Catalytic asymmetric carbonyl addition reactions catalysed by group

... Asymmetric reductive coupling of alkynes and aldehydes 10-12 Nickel-catalysed intermolecular reductive coupling (exclusive cis-addition) of aryl-C≡C-alkyl alkynes with aldehydes can be accomplished in the presence of a catalytic amount of the commercially available (+)-(neomenthyl)-diphenylphosphine ...
Electophilic Aromatic Substituion - Towson University
Electophilic Aromatic Substituion - Towson University

...  The addition of bromine occurs in two steps  In the first step the  electrons act as a nucleophile toward ...
Reactions of Alcohols
Reactions of Alcohols

... • Chloride is a weaker nucleophile than bromide. • Add ZnCl2, which bonds strongly with -OH, to promote the reaction. • The chloride product is insoluble. • Lucas test: ZnCl2 in conc. HCl 1° alcohols react slowly or not at all. 2 alcohols react in 1-5 minutes. 3 alcohols react in less than 1 mi ...
A convenient method for the preparation of oxazaborolidine catalyst
A convenient method for the preparation of oxazaborolidine catalyst

... become an important area of research for pharmaceutical industries, as often two enantiomers of a chiral drug molecule display different biological activities.1 Asymmetric reduction of prochiral ketones is an extremely important methodology for the synthesis of chiral secondary alcohols. The oxazabor ...
Chapter 4 Functional Group Transformations: Oxidation and
Chapter 4 Functional Group Transformations: Oxidation and

Solid-Phase Organic Synthesis: Creation of Carbon
Solid-Phase Organic Synthesis: Creation of Carbon

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Discodermolide



(+)-Discodermolide is a polyketide natural product found to stabilize microtubule. (+)-discodermolide was isolated by Gunasekera and his co-workers at the Harbor Branch Oceanographic Institute from the deep-sea sponge Discodermia dissoluta in 1990. (+)-Discodermolide was found to be a potent inhibitor of tumor cell growth in several MDR cancer cell lines. (+)-discodermolide also shows some unique characters, including a linear backbone structure, immunosuppressive properties both in vitro and in vivo, potent induction of an accelerated senescence phenotype, and synergistic antiproliferative activity in combination with paclitaxel. Discodermolide was recognized as one of the most potent natural promoters of tubulin assembly. A large number of efforts toward the total synthesis of (+)-discodermolide were directed by its interesting biological activities and extreme scarcity of natural sources (0.002% w/w from frozen marine sponge). The compound supply necessary for complete clinical trials cannot be met by harvesting, isolation, and purification. As of 2005, attempts at synthesis or semi-synthesis by fermentation have proven unsuccessful. As a result, all discodermolide used in preclinical studies and clinical trials has come from large-scale total synthesis.
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