The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• selenide. Oxidation and elimination of the corresponding selenoxide at elevated temperature generated the necessary dienophile, which directly underwent an intramolecular endo-Diels–Alder reaction to give the isoindolinone 68. For the synthesis of 69 another ten steps were necessary to discriminate between

• synthesis of cytochalasin D (70), namely oxidation of the selenide to the selenoxide, elimination and intramolecular Diels–Alder reaction, isoindolinone 90 could be obtained in moderate yield. Removal of the protecting groups then yielded aspergillin PZ (91). Though having established a rather long and low

Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

• Qiang Wei,
• Ya-Yi Wang,
• Yu-Liu Du and
• Liu-Zhu Gong

Beilstein J. Org. Chem. 2013, 9, 1559–1564, doi:10.3762/bjoc.9.177

• )-3b. After a single recrystallization from methanol, the product 4a was obtained in 50% yield and with 97% ee. The oxidative deselenation of 4a with MCPBA afforded the corresponding alcohol 5 in 95% yield. The stereochemistry of the alcohol was found to be identical to that of the parent selenide, as

Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides

• Yohsuke Kobiki,
• Shin-ichi Kawaguchi,
• Takashi Ohe and
• Akiya Ogawa

Beilstein J. Org. Chem. 2013, 9, 1141–1147, doi:10.3762/bjoc.9.127

• absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method. Keywords: arylation; unsymmetrical diaryl selenide; free radical; organobismuth; photoinduced reaction; Introduction A number of organoselenium compounds are

• using this mechanism have been reported [55][56]. We presume that a phenyl radical generated from triphenylbismuthine can be captured by organic diselenides, which have a high carbon-radical-capturing ability [57][58][59][60][61][62][63][64] and as a result, diaryl selenide will be generated (Scheme 1

• ). In 1999, Barton and co-workers reported that diaryl selenide was obtained by the reaction of triarylbismuthine with diphenyl diselenide under heating at high temperature (140 °C) [65], but the photoinduced reaction was not investigated. In this letter, we will report the radical reaction of diaryl

Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• including dimethyl diselenide (20) and dimethyl triselenide (21). In addition, the mixed sulfur/selenium compounds dimethylselenyl sulfide (15), bis(methylthio) selenide (16), methylseleno disulfide (17), methyl methylthio diselenide (18), and bis(methylseleno) sulfide (19) were found. A similar headspace

The chemistry of bisallenes

• Henning Hopf and
• Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates

• Xinghua Wu,
• Yu Chen,
• Herve Aloysius and
• Longqin Hu

Beilstein J. Org. Chem. 2011, 7, 1030–1035, doi:10.3762/bjoc.7.117

• Table 1 and Table 2, through the reaction of N-hydroxysuccinimide (HOSu)-activated esters or mixed anhydrides of Nα-protected amino acids with sodium hydrogen selenide to form their corresponding Nα-protected amino selenocarboxylate, followed by the coupling of the selenocarboxylate with p-nitrophenyl

Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

• Satish S. More,
• T. Krishna Mohan,
• Y. Sateesh Kumar,
• U. K. Syam Kumar and
• Navin B. Patel

Beilstein J. Org. Chem. 2011, 7, 831–838, doi:10.3762/bjoc.7.95

• use for the development of novel synthetic methodologies and for various organic transformations. Recently, the ring opening of N-vinyl substituted aziridines by selenide nucleophiles to furnish functionalized open chain compounds has been described [23]. N-vinyl substituted aziridines can be

The allylic chalcogen effect in olefin metathesis

• Yuya A. Lin and
• Benjamin G. Davis

Beilstein J. Org. Chem. 2010, 6, 1219–1228, doi:10.3762/bjoc.6.140

• allyl selenide 28a was found to be more effective than the allyl sulfide case in CM, with respective yields of 72% and 56% (Scheme 11a). The CM reaction with a more complex and biochemically relevant carbohydrate substrate 29 was also examined. Indeed, the allyl selenide was overall more reactive than

• favorable than the sulfur in allyl sulfides. While, as a single example, Kotetsu and co-workers have synthesized selenium-containing bicyclic β-lactams via RCM of an allyl selenide derivative, enhanced reactivity was unnoticed [39]. With a better understanding of the allylic chalcogen effect, olefin

• selenide protein tag is a requirement for most effective CM. Allyl and hexenyl ethers were found to be the most compatible CM partners for allyl sulfide or selenide containing proteins. The more challenging alkene substrates, such as the ones containing electron-deficient N-acetylamine, GlcNAc and

Aromatic and heterocyclic perfluoroalkyl sulfides. Methods of preparation

• Vladimir N. Boiko

Beilstein J. Org. Chem. 2010, 6, 880–921, doi:10.3762/bjoc.6.88

• %) than from the corresponding esters of trifluoromethanesulfonic acid (20–30%). Alkyl thioesters of trifluoroacetic and trifluoromethanesulfonic acids form AlkSCF3 in higher yields (up to 80%). As shown in Scheme 58, the CF3• radical can attack at several sites. Phenyl selenide esters of

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

• of the aziridine. They exploited the presence of a β-dicarbonyl functionality in 71 to introduce a phenylseleno function α to the lactam centre (Scheme 20). Then, hydrolysis of the methyl ester followed by decarboxylation and reduction of the lactam with borane gave the selenide diastereoisomers 72