Synthesis of Betamethasone From the Waste of Thai <i>Agave Sisalana</i>

Kongkathip, Ngampong; Kongkathip, Boonsong; Noimai, Naratitt

doi:10.1080/00397910500464855

Synthetic Communications

2006

DOI: 10.1080/00397910500464855

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Synthesis of Betamethasone From the Waste of Thai Agave Sisalana

Ngampong Kongkathip

Boonsong Kongkathip

Naratitt Noimai

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Cited by 17 publications

(18 citation statements)

References 9 publications

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“…Besides, the C-atom resonances related to ring F, d(C) 26.8 (C(23)), d(C) 26.0 (C(24)), d(C) 27.7 (C(25)), d(C) 65.4 (C(26)), and d(C) 16.5 (C(27)), verified the (25S) configuration [13]. The a-equatorial orientation of HÀC(5) was deduced from the chemical shift of Me (19) at d(C) 18.4 [14] and the a-equatorial orientation of HÀC(3) from the NOESY cross-peak d(H) 3.84(HÀC(3))/d(H) 0.99 (HÀC(5)) [2]. The four anomeric H-and C-atoms in the 1 H-and 13 C-NMR spectrum indicated the presence of four sugar units.…”

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confidence: 67%

“…The resonances at d(C) 44.0 and d(H) 0.87 were attributed to C (13) and Me (18), respectively, on the basis of the HMBCs from d(H) 0.87 to d(C) 44.0 and C (17). Thus the tertiary Me group at d(H) 0.80 was ascribable to Me (19). The HMBC between the Me(19) signal and d(C) 38.5 (C(10)) allowed the determination of the latter.…”

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confidence: 94%

“…The HMBC between the Me(19) signal and d(C) 38.5 (C(10)) allowed the determination of the latter. Moreover, the HSQC showed the correlations d(C) 17.5 (C(18))/d(H) 0.87 (Me(18)), d(C) 18.4 (C(19))/d(H) 0.80 (Me (19)), d(C) 9.3 (C(21))/d(H) 1.17 (Me(21)), and d(C) 16.5 (C(27))/d(H) 1.02 (Me(27)). The location of a C(9)¼C(11) bond was confirmed from the HMBC spectrum displaying correlations from the olefinic H-atom at d(H) 5.39 to the C-atom resonances of C(10) and C (13).…”

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confidence: 99%

“…In particular, henryiosides A(1), B(2), and D(4) are based on steroidal aglycones never reported before. Although the aglycones of henryioside C(3) and E (5) have been synthesized before [18] [19], they are reported in natural products for the first time.…”

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confidence: 99%

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Steroidal Saponins from the Rhizomes of Smilacina henryi

Zhang

Chen

et al. 2013

Helvetica Chimica Acta

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Five steroidal saponins, namely henryiosides A -E (1 -5), were isolated from the EtOH extract of the rhizomes of Smilacina henryi. Their structures were elucidated by the extensive use of 1D-and 2D-NMR experiments, along with HR-MALDI-MS analysis and the results of acid hydrolysis. The aglycones of henryiosides A -E possess a C(7)¼C(8) or C(9)¼C(11) bond and were not previously found in saponins.

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confidence: 67%

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confidence: 94%

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confidence: 99%

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confidence: 99%

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Steroidal Saponins from the Rhizomes of Smilacina henryi

Zhang

Chen

et al. 2013

Helvetica Chimica Acta

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“…available in large quantities from the waste of sisal plants, is known to be used for the synthesis of cortisol 23,24. This is particularly important as sisal, unlike most plants, does not use the C3 (or indeed C4) photosynthetic pathway but instead uses the crassulacean acid metabolism (CAM) pathway.…”

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confidence: 99%

IRMS delta values (¹³C) of nandrolone and testosterone products available in the UK: Implications for anti‐doping

Brailsford

Majidin

Wojek³

et al. 2018

Drug Testing and Analysis

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Anabolic androgenic steroids (AAS) are the most widely abused class of drugs by athletes and thus represent a significant problem to the anti-doping community.Confirmation of a doping violation for AAS cannot always be based on their presence alone due to the endogenous production of some steroids. Both testosterone (and its metabolites) and the major diagnostic metabolite of nandrolone (19-norandrosterone) are produced endogenously. Gas chromatography-combustion-isotope ratio mass spectrometry (GC-C-IRMS) is used in such cases to differentiate between the administration of a synthetic preparation and endogenous steroid production by measurement of their differing carbon isotope ( 13 C/ 12 C) ratio. The purpose of this study was to investigate the availability of steroid preparations in the UK with a 13 C content analytically indistinguishable from that of endogenous steroids. Fourteen preparations containing nandrolone (n = 9) and testosterone (n = 5) were analyzed.The δ 13 C values were determined using GC-C-IRMS and the identity of the steroid preparations was confirmed using gas chromatography-mass spectrometry (GC-MS). Ten steroid preparations displayed δ 13 C values within the range expected for synthetic steroids (less than −27‰). However, four nandrolone preparations displayed δ 13 C values that overlap with the values considered to be endogenous in origin (range: −26 to −16‰). Misuse of these preparations could prevent the confirmation of nandrolone administration using GC-C-IRMS in anti-doping cases.

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Divergent Chemo‐ and Biocatalytic Route to 16β‐Methylcorticoids: Asymmetric Synthesis of Betamethasone Dipropionate, Clobetasol Propionate, and Beclomethasone Dipropionate

Wei,

Zhang,

Liu

et al. 2023

Angewandte Chemie

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Abstract16β‐Methylcorticoids are among the most important glucocorticoid steroids for the treatment of various dermatological disorders, respiratory infections, and other allergic reactions elicited during inflammatory responses of the human body. Betamethasone dipropionate, clobetasol propionate, and beclomethasone dipropionate are particularly noteworthy for their synthetic intractability. Despite five decades of research, these 16β‐methylcorticoids have remained challenging synthetic targets owing to insurmountable issues of reactivity, selectivity, and cost efficiency associated with all previously explored strategies. We herein report our practicability‐oriented strategy toward the unified stereoselective synthesis of 16β‐methylcorticoids in 12.6–14.0 % overall yield from commercially available 9α‐hydroxyandrost‐4‐ene‐3,17‐dione (9α‐OH‐AD). In this approach, the chiral C16β‐Me and C17α‐OH groups of the corticosteroid D ring were installed via a substrate‐controlled diastereo‐ and enantioselective Mn‐catalyzed oxidation‐reduction hydration of Δ4,9(11),16‐triene‐3,20‐dione. The C1−C2 double bond of the corticosteroid A ring was constructed using an unprecedented engineered 3‐ketosteroid‐Δ1‐dehydrogenase (MK4‐KstD)‐catalyzed regioselective Δ1‐dehydrogenation of Δ4,9(11)‐diene‐3,21‐dione. This strategy provides a general method and a key precursor for the divergent synthesis of a variety of glucocorticoids and related steroidal drugs.

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Synthesis of Betamethasone From the Waste of Thai Agave Sisalana

Cited by 17 publications

References 9 publications

Steroidal Saponins from the Rhizomes of Smilacina henryi

Steroidal Saponins from the Rhizomes of Smilacina henryi

IRMS delta values (¹³C) of nandrolone and testosterone products available in the UK: Implications for anti‐doping

Divergent Chemo‐ and Biocatalytic Route to 16β‐Methylcorticoids: Asymmetric Synthesis of Betamethasone Dipropionate, Clobetasol Propionate, and Beclomethasone Dipropionate

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Synthesis of Betamethasone From the Waste of Thai Agave Sisalana

Cited by 17 publications

References 9 publications

Steroidal Saponins from the Rhizomes of Smilacina henryi

Steroidal Saponins from the Rhizomes of Smilacina henryi

IRMS delta values (13C) of nandrolone and testosterone products available in the UK: Implications for anti‐doping

Divergent Chemo‐ and Biocatalytic Route to 16β‐Methylcorticoids: Asymmetric Synthesis of Betamethasone Dipropionate, Clobetasol Propionate, and Beclomethasone Dipropionate

Contact Info

Product

Resources

About

IRMS delta values (¹³C) of nandrolone and testosterone products available in the UK: Implications for anti‐doping