One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

• Giovanna Bosica,
• Kaylie Demanuele,
• José M. Padrón and
• Adrián Puerta

Beilstein J. Org. Chem. 2020, 16, 2862–2869, doi:10.3762/bjoc.16.235

• the pharmaceutical industry [3][8]. An analysis of the market shows that there are over 7000 drugs derived from dihydropyridines, some of which are blockbuster drugs, such as Tamiflu®, dioscorine, ibogaine, and isoquinuclidines [9][10]. Classically the Hantzsch synthesis involved the condensation of 2

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

• Cloudius R. Sagandira and
• Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

• Cloudius R. Sagandira Paul Watts Nelson Mandela University, University Way, Port Elizabeth, 6031, South Africa 10.3762/bjoc.15.251 Abstract Tamiflu is one of the most effective anti-influenza drugs, which is currently manufactured by Hoffmann-La Roche from shikimic acid. Owing to its importance

• explosive azide chemistry involved in a proposed Tamiflu route by taking advantage of the continuous-flow technology. The azide intermediates were safely synthesised in full conversions and >89% isolated yields. Keywords: azide chemistry; continuous flow synthesis; hazardous; safe; Tamiflu; Introduction

• Tamiflu is currently one of the most important drugs available to combat the influenza virus and this has seen immense research efforts by the scientific community to exclusively focus on the development of new, better and practical approaches to manufacture this drug [1][2]. More than 60 synthetic routes

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

• Yan Li,
• Xue Zhou,
• Guangfan Zheng and
• Qian Zhang

Beilstein J. Org. Chem. 2015, 11, 2721–2726, doi:10.3762/bjoc.11.293

• ; Findings Direct aminooxygenation of alkenes provides a straightforward and powerful approach to construct the 1,2-aminoalcohol skeleton [1], which is ubiquitous in bioactive compounds (such as the drugs bestatin (1) and tamiflu (2), the natural products Al-77-B (3) and hapolosin (4); Figure 1) [2] and has

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

• Yiyang Liu,
• Marc Liniger,
• Ryan M. McFadden,
• Jenny L. Roizen,
• Jacquie Malette,
• Corey M. Reeves,
• Douglas C. Behenna,
• Masaki Seto,
• Jimin Kim,
• Justin T. Mohr,
• Scott C. Virgil and
• Brian M. Stoltz

Beilstein J. Org. Chem. 2014, 10, 2501–2512, doi:10.3762/bjoc.10.261

• (−)-dragmacidin F [38][39][40][41], and the initial commercial-scale synthesis of Tamiflu [42]. In Renaud’s formal total synthesis of (−)-quinic acid (21) [35], a key carboxylic acid 22 was accessed, intercepting Novak’s older synthesis of the natural product (Scheme 4) [36]. To begin, Renaud transformed the

Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

• Melinda Nonn,
• Loránd Kiss,
• Reijo Sillanpää and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2012, 8, 100–106, doi:10.3762/bjoc.8.10

• molecules such as β-hydroxyketones [7][8][9][10], amino alcohols or amino acids [11][12][13][14][15][16][17], etc. The multifunctionalized cyclic amino acids – e.g., the antibiotic Oryzoxymycin [18][19][20][21], the antiviral agents Tamiflu [22][23][24][25][26][27][28][29][30][31][32][33], Zanamivir and 2,3