Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• approach this ideal, representing a reactivity-based concept where reactive functionalities are generated and consumed in each step [24]. MCR can be conducted in a domino, sequential, or consecutive fashion, offering a versatile approach to synthetic design by creating countless new sequences by

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• ) was different from the value reported for the natural product ([α]D −100, c 0.015, CHCl3) [16] and hypothesized that the configuration of the natural compound would be 3S,4R, different from that reported in the Pettit previous work. Couladouros and co-workers based the synthetic design of

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

• Mysore Bhyrappa Harisha,
• Pandi Dhanalakshmi,
• Rajendran Suresh,
• Raju Ranjith Kumar and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

• precursor for nitrogen heterocycles. As a part of our synthetic design towards the construction of five-membered heterocycles, we have previously reported the synthesis of highly substituted imidazoles [6], indoles [7] and pyrroles [8] starting from different azidochalcones. In continuation, employing α

Multicomponent reactions III

• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1974–1975, doi:10.3762/bjoc.15.192

• environmental concern, the concept of multicomponent reactions (MCRs) [1] has become a particularly powerful principle of synthetic design, combining synthetic efficiency with conceptual efficacy. The importance of rapid lead finding and identification has demanded novel ways of synthetic approaches, ultimately

Gram-scale preparation of negative-type liquid crystals with a CF₂CF₂-carbocycle unit via an improved short-step synthetic protocol

• Tatsuya Kumon,
• Shohei Hashishita,
• Takumi Kida,
• Shigeyuki Yamada,
• Takashi Ishihara and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 148–154, doi:10.3762/bjoc.14.10

• improved methodology enables us to prepare the CF2CF2-containing cyclohexadiene 1a and the corresponding cyclohexane 2c, as selected examples, on the multigram scale. Results and Discussion Improved synthetic design In order to establish an improved synthetic protocol, we initially designed a method for

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• with the same aglycon leaving group can be used enabling an iterative glycosylation, simplifying the overall synthetic design. For a preactivation based glycosylation reaction to be successful the intermediate formed upon preactivation must be stable prior to the addition of the acceptor and yet

Accessing simply-substituted 4-hydroxytetrahydroisoquinolines via Pomeranz–Fritsch–Bobbitt reaction with non-activated and moderately-activated systems

• Marco Mottinelli,
• Mathew P. Leese and
• Barry V. L. Potter

Beilstein J. Org. Chem. 2017, 13, 1871–1878, doi:10.3762/bjoc.13.182

• factors controlling the regiochemical outcome of the reaction to direct synthetic design. Reaction conditions of the PFB methodology and opportune modifications necessary to direct such reactions towards the synthesis of the desired THIQ derivatives are reported here. Results and Discussion To address

A new and expeditious synthesis of all enantiomerically pure stereoisomers of rosaprostol, an antiulcer drug

• Wiesława Perlikowska,
• Remigiusz Żurawiński and
• Marian Mikołajczyk

Beilstein J. Org. Chem. 2016, 12, 2234–2239, doi:10.3762/bjoc.12.215

• ; stereoselective synthesis; synthetic design; Introduction Rosaprostol (1) is a trade name for 7-(2-hexyl-5-hydroxycyclopentane)heptanoic acid (Figure 1) which belongs to a series of 19,20-dinorprostanoic acid derivatives. It exhibits gastric antisecretory activity and cytoprotective action without the undesired

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• philosophy for synthetic design that was derived from Roald Hoffmann’s idea of chemistry being “the same and not the same” [9]. At around this time (2006), click chemistry [10] (Figure 3) had caught my attention for its prevalence but I did not know why it was being used so much. All I could venture was that

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• Discussion Synthetic design The fluorescent probes were designed as analogues of the best multivalent pharmacological chaperones/correctors reported so far that typically display three to four copies of a DNJ ligand linked to a central core via an alkyl chain spacer (Figure 1) [24][25][26]. The choice of the

Transition-metal and organocatalysis in natural product synthesis

• David Yu-Kai Chen and
• Dawei Ma

Beilstein J. Org. Chem. 2013, 9, 1192–1193, doi:10.3762/bjoc.9.134

• and inspire further investigations in this field, and challenge the existing technologies and our current mindset in target-oriented synthetic design. Ultimately, we wish that the newly acquired knowledge will translate to further advances in synthetic organic chemistry and provide more enabling tools

Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis

• Aleksey I. Gerasyuto,
• Zhi-Xiong Ma,
• Grant S. Buchanan and
• Richard P. Hsung

Beilstein J. Org. Chem. 2013, 9, 1170–1178, doi:10.3762/bjoc.9.131

• ][63], and tubulosine [64]. With the appropriate choice of an R group in the synthetic design, a highly convergent and expedient strategy can come forth for constructing these alkaloids. We report herein our success in achieving intramolecular aza-[3 + 3] annulations of an enone. Results and Discussion

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• developing a cost-effective method, this option was not pursued. Changing the 4-oxy substituent In terms of synthetic design, the 4-methoxy substituent was envisaged as having implications for reactivity of the silyloxypyrrole as well as relevance to installation of the C-1 hydroxyl in a convergent