Synthesis of exemestane labelled with 13C

Fontana, E.; Pignatti, A.; Giribone, D.; Salle, E. Di

doi:10.1016/j.steroids.2008.02.010

Cited by 6 publications

(2 citation statements)

References 14 publications

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“…Two synthetic routes to [3,4- 13 C2]-enriched and [2,3,4- 13 C3]-enriched steroids have been previously reported. In the first one, the enone of the A-ring of ADD was opened either by ozonolysis followed by treatment with hydrogen peroxide or by oxidative cleavage with KMnO 4 /KIO 4 .…”

Section: Introductionmentioning

confidence: 99%

Hemisynthesis of 2,3,4-¹³C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of ¹³C3-Androstanes and ¹³C3-Estranes

et al. 2018

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In this contribution, we describe two simple and efficient routes for the preparation of keto-aldehyde 1, a key intermediate for the synthesis of C3-androstanes andC3-estranes. In the first route, the targeted aldehyde 1 was obtained in 40% overall yield from 1,4-androstadien-3,17-dione (3 mmol scale) via a two-step sequence involving a one-pot, abnormal ozonolysis/sulfur oxidation/retro-Michael/ozonolysis process. Alternatively, a second route from 4-androsten-3,17-dione, using a six-step sequence, was optimized to produce 40 mmol batches of the key intermediate 1 in 42% overall yield. At the final stage, the A-ring was reconstructed through a Wittig reaction with the 1-triphenylphosphoranylidene-C3-2-propanone 2, followed by an intramolecular condensation assisted by thioacetic acid via a Michael addition/retro-Michael reaction sequence to provide 2,3,4-C3-1,4-androstadien-3,17-dione.

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Section: Introductionmentioning

confidence: 99%

Hemisynthesis of 2,3,4-¹³C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of ¹³C3-Androstanes and ¹³C3-Estranes

et al. 2018

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“…one 40 (Scheme 5). 29 Exemestane, marketed under the name Aromasinr® (FDA approval on October 21, 1999), was the first oral aromatase inactivator approved for the treatment of advanced breast cancer in postmenopausal women resistant to tamoxifen therapy. In this synthesis, the two 13 C atoms at C3 and C4 were incorporated using acylation of enol lactone 41 with [1,2-13 C 2 ]AcCl, followed by hydrolysis, decarboxylation, and cyclization to reconstruct the A ring.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of 13C-Labeled Steroids

Dénès

Farard²,

Lebreton

2019

Synthesis

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Due to the wide spectrum of biological activities of steroids, the detection and quantification of steroidal residues in various biological materials are crucial for drug development, doping prevention, and environmental protection. In addition, the analytical technique of stable isotopic dilution (SID) by Liquid Chromatography-Mass Spectrometry (LC-MS) requires 13C-labeled steroids as standards to provide accurate and reproducible steroid quantification. In this context, the synthesis of 13C-labeled steroids is reviewed. The approaches based on partial synthesis starting from commercially available steroids have been, by far, the most commonly employed strategy.1 Introduction2 Hemisynthesis of 13C3-Labeled Steroids via Partial Degradation of the A Ring2.1 Degradation of the A Ring to an Enol Lactone2.1.1 Introduction of 13C Atom(s) via Claisen Condensation: Turner’s Strategy2.1.2 Introduction of 13C Atom(s) with 13C-Labeled 5-(Diethylphosphono)pentan-2-one Ethylene Ketal Based on the Fujimoto–Belleau Reaction2.2 Degradation of the A Ring and Introduction of 13C Atom(s) with [13C3]-1-(Triphenylphosphoranylidene)propan-2-one3 Construction of the A Ring from an α,β-Unsaturated Ketone with 13C-Labeled 1-Iodo-3,3-(ethylenedioxy)butane as Electrophile4 Construction of the A and B rings: Stork’s Strategy5 Hemisynthesis with Introduction of 13C Atom(s) in the C17 Side Chain6 Conclusion

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Increased yield of biotransformation of exemestane with β-cyclodextrin complexation technique

Deng

et al. 2013

Steroids

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Synthesis of exemestane labelled with 13C

Cited by 6 publications

References 14 publications

Hemisynthesis of 2,3,4-¹³C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of ¹³C3-Androstanes and ¹³C3-Estranes

Hemisynthesis of 2,3,4-¹³C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of ¹³C3-Androstanes and ¹³C3-Estranes

Synthesis of 13C-Labeled Steroids

Increased yield of biotransformation of exemestane with β-cyclodextrin complexation technique

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Synthesis of exemestane labelled with 13C

Cited by 6 publications

References 14 publications

Hemisynthesis of 2,3,4-13C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of 13C3-Androstanes and 13C3-Estranes

Hemisynthesis of 2,3,4-13C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of 13C3-Androstanes and 13C3-Estranes

Synthesis of 13C-Labeled Steroids

Increased yield of biotransformation of exemestane with β-cyclodextrin complexation technique

Contact Info

Product

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Hemisynthesis of 2,3,4-¹³C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of ¹³C3-Androstanes and ¹³C3-Estranes

Hemisynthesis of 2,3,4-¹³C3-1,4-Androstadien-3,17-dione: A Key Precursor for the Synthesis of ¹³C3-Androstanes and ¹³C3-Estranes