Polymer-supported selenium reagents for organic synthesis

Nicolaou, K. C.; Pastor, Joaquı́n; Barluenga, Sofía; Winssinger, Nicolas

doi:10.1039/a804795b

Cited by 158 publications

(120 citation statements)

References 15 publications

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“…[90]). Nicolaou's group then proceeded to develop the nec-G. M. CRAGG AND D. J. NEWMAN essary solid-phase synthetic methods by modifying a reagent that they had reported in the literature a couple of years earlier, a polystyrene-based selenenyl bromide resin [93]. Application of this methodology has led to the identification and subsequent optimization of benzopyrans with a cyanostilbene substitution that are effective against vancomycin-resistance bacteria (Fig.…”

Section: Combinatorial Chemistry and Natural Productsmentioning

confidence: 97%

Biodiversity: A continuing source of novel drug leads

Cragg

Newman

2005

Pure and Applied Chemistry

311

219

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Nature has been a source of medicinal agents for thousands of years and continues to be an abundant source of novel chemotypes and pharmacophores. With only 5 to 15 % of the approximately 250 000 species of higher plants systematically investigated, and the potential of the marine environment barely tapped, these areas will remain a rich source of novel bioactive compounds. Less than 1 % of bacterial and 5 % of fungal species are currently known, and the potential of novel microbial sources, particularly those found in extreme environments, seems unbounded. To these natural sources can be added the potential to investigate the rational design of novel structure types within certain classes of microbial metabolites through genetic engineering. It is apparent that Nature can provide the novel chemical scaffolds for elaboration by combinatorial approaches (chemical and biochemical), thus leading to agents that have been optimized on the basis of their pharmacological activities. The proven natural product drug discovery track record, coupled with the continuing threat to biodiversity through the destruction of terrestrial and marine ecosystems and the current low number of new chemical entities in pharmaceutical industry pipelines, provides a compelling argument in favor of expanded multidisciplinary and international collaboration in the exploration of Nature as a source of novel leads for the development of drugs and other valuable bioactive agents. BIODIVERSITY: MEDICINALS FOR THE MILLENNIA Recorded historyThroughout the ages, humans have relied on Nature for their basic needs for the production of foodstuffs, shelters, clothing, means of transportation, fertilizers, flavors and fragrances, and, not least, medicines. Plants have formed the basis of sophisticated traditional medicine systems that have been in existence for thousands of years. The first records, written on clay tablets in cuneiform, are from Mesopotamia and date from about 2600 B.C.; among the substances they used were oils of Cedrus species (cedar) and Cupressus sempervirens (cypress), Glycyrrhiza glabra (licorice), Commiphora species (myrrh), and Papaver somniferum (poppy juice), all of which are still in use today for the treatment of ailments ranging from coughs and colds to parasitic infections and inflammation. Egyptian medicine dates from about 2900 B.C., but the best known Egyptian pharmaceutical record is the Ebers Papyrus dating from 1500 B.C.; this documents some 700 drugs (mostly plants), and includes formulas, such as gargles, snuffs, poultices, infusions, pills, and ointments, with beer, milk, wine, and honey being commonly used as vehicles. The Chinese Materia Medica has been extensively documented over

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Section: Combinatorial Chemistry and Natural Productsmentioning

confidence: 97%

Biodiversity: A continuing source of novel drug leads

Cragg

Newman

2005

Pure and Applied Chemistry

311

219

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“…127 The advantage of this reagent is the convenience of handling and the lack of odor when compared with the nonbound reagents.…”

mentioning

confidence: 99%

Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

138

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The current interest in solid-phase organic synthesis has led to a renewed interest in a complementary technique in which solid supported reagents are used in solution phase chemistry. This technique obviates the need for attachment of the substrate to a solid-support, and enables the chemist to monitor the reactions using familiar analytical techniques. The purpose of this review is to increase awareness of the wide range of useful transformations which can be accomplished using solid-supported reagents.

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“…[6][7][8][9] An alternative is the "traceless" linker 10 introduced by Ellman, [11][12] traditionally substituting a C-Si bond by C-H upon cleavage. Carbon-sulfur and carbon-selenium bonds offer additional possibilities 13 for traceless cleavage, as illustrated by recent publications by Ruhland, 14 Nicolaou,15 and Fujita. 16 Here, we report our complementary synthesis of a selenide linker.…”

Section: Introductionmentioning

confidence: 89%

A selenide linker for “traceless” solid-phase organic synthesis

Kulkarni

Ganesan

2000

Biotechnol. Bioeng.

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4‐Bromophenethyl alcohol was protected as the THP ether, followed by reaction with magnesium and selenium to give the corresponding diselenide. Ether deprotection provides a diselenide diol, which is attached to solid‐phase resins. The polymer‐bound selenide anion is then generated, and functions as a traceless linker for electrophiles such as alkyl halides. © 2001 John Wiley & Sons, Inc. Biotechnol Bioeng (Comb Chem) 71:104–106, 2000/2001.

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Polymer-supported selenium reagents for organic synthesis

Abstract: Organoselenium resins 1–4 were prepared from polystyrene via lithiation and quenching with MeSeSeMe, and shown to react with a variety of substrates, aiding in useful functionalizations

Cited by 158 publications

References 15 publications

Biodiversity: A continuing source of novel drug leads

Biodiversity: A continuing source of novel drug leads

Solid-supported reagents in organic synthesis

A selenide linker for “traceless” solid-phase organic synthesis

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