Process Development of Tacalcitol

Lee, Seung Jong; Moon, Hyung Wook; Lee, Kee‐Young; Oh, Chang‐Young; Kim, U Bin; Shin, Hyunik

doi:10.1021/acs.oprd.1c00010

Cited by 4 publications

(3 citation statements)

References 27 publications

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“…Also in this case, both the HWE and Wittig reaction failed to provide the key steroidal intermediate 32 (data not shown). Thus, 2-((2-(2-methyl-2Htetrazol-5-yl)ethyl)sulfonyl)benzo[d]thiazole (36) (Scheme 6B) was prepared 23 and reacted with the C22-aldehyde 17 to give olefin 32 in 24% yield (E/Z ratio: 7/3) (Scheme 7). Compound 32 was hydrogenated with Pd/C in THF and finally submitted to Jones oxidation leading the desired 24-(N-2-methyl-tetrazol-5-yl)-5α-chol-7-en-3-one (12) in 44% yield.…”

Section: Resultsmentioning

confidence: 99%

Discovery and Structure–Activity Relationships of Novel ssDAF-12 Receptor Modulators

Ceccarelli,

Goracci,

Carotti

et al. 2024

J. Med. Chem.

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The nuclear receptor ssDAF-12 has been recognized as the key molecular player regulating the life cycle of the nematode parasite Strongyloides stercoralis. ssDAF-12 ligands permit the receptor to function as an on/off switch modulating infection, making it vulnerable to therapeutic intervention. In this study, we report the design and synthesis of a set of novel dafachronic acid derivatives, which were used to outline the first structure−activity relationship targeting the ssDAF-12 receptor and to unveil hidden properties shared by the molecular shape of steroidal ligands that are relevant to the receptor binding and modulation. Moreover, biological results led to the discovery of sulfonamide 3 as a submicromolar ssDAF-12 agonist endowed with a high receptor selectivity, no toxicity, and improved properties, as well as to the identification of unprecedented ssDAF-12 antagonists that can be exploited in the search for novel chemical tools and alternative therapeutic approaches for treating parasitism such as Strongyloidiasis.

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Section: Resultsmentioning

confidence: 99%

Discovery and Structure–Activity Relationships of Novel ssDAF-12 Receptor Modulators

Ceccarelli,

Goracci,

Carotti

et al. 2024

J. Med. Chem.

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“…Shin et al . reported that the synthesis of Tacalcitol 225 was achieved via Julia‐Kocienski olefination [66] . The intermediate product 228 was reacted with β‐oxybenzothiazol‐2‐yl sulfone 227 under Julia‐Kocienski reaction conditions and gave the desired E ‐olefine 224 a in 87 % yield.…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

“…Shin et al reported that the synthesis of Tacalcitol225 was achieved via Julia-Kocienski olefination. [66] The intermediate product 228 was reacted with β-oxybenzothiazol-2-yl sulfone 227 under Julia-Kocienski reaction conditions and gave the desired E-olefine 224 a in 87 % yield. This resultant product was purified by flash chromatography and then was subjected toa sequence of chemical reactions such as HWE (Horner-Wadsworth-Emmons) reaction, deprotection and oxidation of hydroxyl groups, etc., to give the Tacalcitol 225.This compound was recrystallized by using MeOH/H 2 O solution to yield Tacalcitol monohydrate (Scheme 43).…”

Section: Synthesis Of Miscellaneous Compoundsmentioning

confidence: 99%

Recent Applications and Trends in the Julia‐Kocienski Olefination

Rinu¹,

Radhika²,

Anilkumar³

2022

ChemistrySelect

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The Julia-Kocienski (J-K) olefination is a modified version of Julia-Lythgoe olefination. In this reaction, an aldehyde or ketone is coupled with heterocycle-bearing sulfone in the presence of a strong base to yield alkene. It has shown wide application in the synthesis of olefinic fragments in natural product synthesis. The Julia-Kocienski olefination is one of the most efficient protocols for the synthesis of E-alkenes. Nowa-days, a variety of natural products were synthesised by using the Julia-Kocienski olefination as the key step, and several developments and modifications were witnessed in this area. This review comprehends the recent developments and achievements in Julia-Kocienski olefination along with its application in natural product synthesis covering literature from 2016 to 2021.

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Julia‐Kocienski Olefination: A Tutorial Review

et al. 2023

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Over the past two decades, Julia‐Kocienski olefination has become one of the most powerful and reliable C=C double‐bond construction methods typically furnishing E‐configured alkenes. This review summarizes the scientific literature of the past decade focusing on the key aspects for successful execution of the olefination step. The main stereoselectivity and yield‐determining aspects have been outlined in separate chapters providing all the necessary information for the synthesis of Julia‐Kocienski reagents as well as the most commonly used reaction optimization techniques.

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Process Development of Tacalcitol

Cited by 4 publications

References 27 publications

Discovery and Structure–Activity Relationships of Novel ssDAF-12 Receptor Modulators

Discovery and Structure–Activity Relationships of Novel ssDAF-12 Receptor Modulators

Recent Applications and Trends in the Julia‐Kocienski Olefination

Julia‐Kocienski Olefination: A Tutorial Review

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