A facile two-step high yield approach to 2-oxasteroids

Frimer, Aryeh A.; Hameiri-Buch, Judith; Ripshtos, Shlomo; Gilinsky-Sharon, Pessia

doi:10.1016/s0040-4020(01)88175-8

Cited by 22 publications

(10 citation statements)

References 28 publications

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“…Finally, we focused on synthesis of newly isolated peribysins O–Q. For this purpose, iodoenone 15b obtained during the diastereomeric separation was treated with KO t Bu and 18-crown-6 under an oxygen atmosphere to afford enol 25 , which upon Suzuki cross coupling followed by TBS deprotection furnished peribysin Q ( 9 ). All of the NMR spectral data were in complete agreement with the reported ones, but the specific optical rotation was found to be exactly opposite.…”

mentioning

confidence: 99%

Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G

et al. 2020

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Herein we report the stereochemical revision of peribysins A, B, C, F, and G, guided by enantiospecific total synthesis starting from (+)-nootkatone. Furthermore, we reconfirmed the absolute stereochemistry of peribysin Q. The highlights of the synthesis are enone transposition and kinetic iodination resulting in separation of diastereomers. Our findings coupled with synthetic and biological data previously reported by Danishefsky's group suggest that the original stereochemistries of peribysins A, B, C, F, and G were misassigned.

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confidence: 99%

Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G

et al. 2020

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“…As part of an ongoing study on androgens 1 and their 2-oxa analogues, 2 the crystal structures of 2-oxa-4-androstene-3,17-dione 1 3 and 6a-hydroxy-2-oxa-4-androstene-3,17-dione 2 2 were determined. Crystals of these compounds were obtained from EtOAc-MeOH mixtures.…”

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confidence: 99%

Isostructurality in crystalline oxa-androgens: a case of C–O–H···O and C–H···O interaction mimicry and solid solution formation

Addlagatta¹,

Nangia²,

Desiraju³

et al. 1998

Chem. Commun.

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“…The desired A-ring fused steroidal pyrazines could be obtained from compound 3 or 7 in quite low yields, without the α-ketoenol intermediates (4 or 8), even in harsh reaction conditions (sulfur and refluxing morpholine) [30]. However, the corresponding α-ketoenols might be prepared in complex reaction conditions, according to previous reports [35,36], such as in dry toluene at −25 • C for 1.5-4 h with t-BuOK (1.5 equiv.) and (3 equiv.)…”

Section: Discussionmentioning

confidence: 84%

Design, Synthesis, and Biological Evaluation of Two Series of Novel A-Ring Fused Steroidal Pyrazines as Potential Anticancer Agents

Wang

Yuan

Qian

et al. 2020

IJMS

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Background: Increasingly, different heterocyclic systems have been introduced into the steroid nucleus to significantly enhance the antitumor activities of steroid molecules. However, in this study, few literature precedents describing the pyrazine heterocyclic-condensed modification to an A-ring of steroid monomers were found, although the pyrazine group is thought to be essential for the potent anticancer activity of clinically relevant drugs and natural steroid dimers. Methods and Results: Two series of novel A-ring fused steroidal pyrazines were designed and efficiently synthesized from commercially available progesterone via key α-ketoenol intermediates. Through a cell counting kit-8 cytotoxic assay of 36 derivatives for three tumor cells, 14 compounds displayed significant antiproliferative activity compared to 5-fluorouracil, especially for human prostatic tumor cells (PC-3) in vitro. Further mechanistic studies indicated that the most active compound, 12n (IC 50 , 0.93 µM; SI, 28.71), could induce the cell apoptosis of PC-3 cells in a dose-dependent manner and cause cell cycle arrest in the G2/M phase. The molecular docking study suggested that compound 12n fitted the active sites of cytochrome P450 17A1 (6CIZ) well. Conclusions: 12n might serve as a promising lead compound for the development of novel anticancer drugs. This facile ring-closing strategy may provide a novel and promising avenue for the cycloaddition reaction of the steroidal skeleton through α-ketoenol intermediates.

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A facile two-step high yield approach to 2-oxasteroids

Cited by 22 publications

References 28 publications

Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G

Overturning the Peribysin Family Natural Products Isolated from Periconia byssoides OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G

Isostructurality in crystalline oxa-androgens: a case of C–O–H···O and C–H···O interaction mimicry and solid solution formation

Design, Synthesis, and Biological Evaluation of Two Series of Novel A-Ring Fused Steroidal Pyrazines as Potential Anticancer Agents

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