Study for diastereoselective aldol reaction in flow: synthesis of (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid, a key component of cyclodepsipeptide HDAC inhibitors

Doi, Takayuki; Otaka, Hiroyuki; Umeda, Koji; Yoshida, Masahito

doi:10.1016/j.tet.2015.05.051

Cited by 14 publications

(7 citation statements)

References 56 publications

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“…In 2015, the diastereoselective synthesis of (E,S)-3-hydroxy-7tritylthio-4-heptenoic acid 43, a key component of cyclodepsipeptide histone deacetylase (HDAC) inhibitors, was achieved in flow (Scheme 4) [99]. Acetyloxazolidinone 41 was used as a chiral auxiliary which was then removed by hydrolysis in the final step of the overall seven-step synthesis.…”

Section: Condensation Reactionsmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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Section: Condensation Reactionsmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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“…[133] In another example, Doi et al reported a flow synthesis of a key intermediate of cyclodepsipeptide histone deacetylase inhibitors. [134] The procedure included a concatenated system for the 1,4-addition of a thiol using acrolein as a Michael acceptor, directly followed with a HWE reaction to deliver α, -unsaturated ester 211 (Figure 56). The upstream section of the reactor The reactor effluent was next mixed and reacted with phosphoacetate anion 210 to trigger a HWE reaction at room temperature.…”

Section: Horner-wadsworth-emmons Olefinationmentioning

confidence: 99%

“…Telescoped continuous flow 1,4-addition/HWE olefination sequence towards α, -unsaturated ester. [134] Ogasawara and Hayashi designed a fully concatenated continuous flow system for the synthesis of (-)-oseltamivir 220, a potent drug for the treatment of influenza. [135] The process relied on five units for the preparation of 220 ( Figure 57).…”

Section: Horner-wadsworth-emmons Olefinationmentioning

confidence: 99%

Continuous Flow Organophosphorus Chemistry

2020

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Organophosphorus derivatives are widespread compounds that chemists find from the bench to the plant, with numerous daily life applications. Besides their common utility for a wide range of notorious reactions such as the Wittig and Horner‐Wadsworth‐Emmons olefinations, the Arbuzov reaction, the Staudinger reaction, the Mitsunobu reaction as well as ligands for a large variety of organometallic complexes, organophosphorus compounds have also found numerous applications as active pharmaceutical ingredients and agrochemicals. Some organophosphorus derivatives are also infamously known as Chemical Warfare Agents. Within the context of generalized adoption of new process technologies in the Chemistry Toolbox, this review intends to give an update on the most recent and significant advances in continuous flow organophosphorus chemistry. Selected examples in methodology, total synthesis and for the preparation of industrially relevant targets are discussed for illustrating the assets of flow chemistry.

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“…Continuous flow chemistry can be used to perform the Horner-Wadsworth-Emmons reaction; Doi and co-workers synthesized a (E)-monofluoroalkene using this strategy (Scheme 42). 55 Wang and co-workers developed a Horner-Wadsworth-Emmons olefination using benzaldehyde, cesium carbonate, and monofluoro-substituted arylmethylphosphonates to give the corresponding monofluoroalkenes in good yields and with poor Z/E selectivity (Scheme 43). 56 The Rolando group used a new phosphonate, S-ethyl 2-(diethoxyphosphoryl)-2-fluorothioacetate, in the Horner-Wadsworth-Emmons reaction.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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Study for diastereoselective aldol reaction in flow: synthesis of (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid, a key component of cyclodepsipeptide HDAC inhibitors

Cited by 14 publications

References 56 publications

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Continuous Flow Organophosphorus Chemistry

Synthesis of Monofluoroalkenes: A Leap Forward

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