A new approach towards the synthesis of drospirenone and steroidal spirolactones

Santhamma, Bindu; Acosta, Kirk; Chávez‐Riveros, Alejandra; Nickisch, Klaus

doi:10.1016/j.steroids.2015.07.008

Cited by 8 publications

(4 citation statements)

References 10 publications

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“…Elution with 60% ethyl acetate in petroleum ether afforded 3β,9α-dihydroxy-17a-oxa-D-homo-5α-androstan-17-one 8 (76mg, 8%) 7 which was identified by comparison of the spectral data to that of an authentic sample. consistent with the presence of a spiro-carbon [18] as was the downfield shift (4.63 ppm) for carbon 8. This suggested that a more thermodynamically stable 5-ring lactone had been formed; this was fully supported by the downfield shift of 6.04 ppm for the C-17 nonprotonated carbon.…”

Section: Transformation Of 3α-acetoxy-17a-oxa-d-homo-5α-androstan-17-supporting

confidence: 72%

Metabolism of steroidal lactones by the fungus Corynespora cassiicola CBS 161.60 results in a mechanistically unique intramolecular ring-D cyclization resulting in C-14 spiro-lactones

Hunter

Oni

Dodd

et al. 2017

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

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Section: Transformation Of 3α-acetoxy-17a-oxa-d-homo-5α-androstan-17-supporting

confidence: 72%

Metabolism of steroidal lactones by the fungus Corynespora cassiicola CBS 161.60 results in a mechanistically unique intramolecular ring-D cyclization resulting in C-14 spiro-lactones

Hunter

Oni

Dodd

et al. 2017

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

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“…Santhamma et al developed another route for steroidal spiro-γ-lactones at C-17, from estran-17-one and androstane-17-one derivatives [ 19 ]. The steroidal 17-ketones were first alkylated in the presence of the lithium derivative of ethyl propiolate.…”

Section: Reviewmentioning

confidence: 99%

Syntheses and medicinal chemistry of spiro heterocyclic steroids

Romero-Hernández,

Ahuja-Casarín,

Merino-Montiel

et al. 2024

Beilstein J. Org. Chem.

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There is compelling evidence that incorporating a heterocyclic moiety into a steroid can alter its pharmacological and pharmacokinetic properties, driving intense interest in the synthesis of such hybrids among research groups. In this review, we present an overview of recent synthetic methodologies, spanning the period from 2000 to 2023, for the preparation of spiro heterocyclic steroids. The compounds surveyed encompass four-, five-, six-, and seven-membered heterocycles appended to various positions of steroidal backbones, with spirocycles containing oxygen, nitrogen, and sulfur atoms being predominant. The outlined synthetic procedures emphasize the pivotal steps for constructing the heterocycles, often accompanied by a detailed account of the overall synthesis pathway. The review encompasses innovative compounds, including bis-steroids linked by a spiro heterocycle and steroids conjugated to heterocyclic moieties containing three or more (hetero)cycles. Moreover, many compounds are accompanied by data on their biological activities, such as antiproliferative, antimalarial, antimicrobial, antifungal, steroid antagonist, and enzyme inhibition, among others, aimed at furnishing pertinent insights for the future design of more potent and selective drugs.

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“…[18,22] The gem-dichlorocyclopropanation of 2 a and 4 a were successfully achieved to furnish medicinally-relevant bicyclo[3.1.0]hexane cores 11 and 12 in excellent yields, respectively. [23] Furthermore, complex tricyclic 5-6-5 fused rings 13 and 14 could be readily synthesized using 1,3-cyclohexanedione. [24] Scheme 5.…”

Section: Forschungsartikelmentioning

confidence: 99%

Ligand‐Controlled Regiodivergence in Nickel‐Catalyzed Vinylcyclopropane Rearrangement

et al. 2023

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A ligand-controlled regiodivergence in Nicatalyzed rearrangement of vinylcyclopropanes to 1,4or 1,5-disubstituted cyclopentenes is reported. The 1,4or 1,5-disubstituted cyclopentene is selectively obtained depending on the choice of ligands. Detailed kinetic studies and density functional theory calculations on the catalytic cycle revealed that the product selectivity is determined at the reductive elimination step from the six-membered η 1 -allyl intermediate.

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A new approach towards the synthesis of drospirenone and steroidal spirolactones

Cited by 8 publications

References 10 publications

Metabolism of steroidal lactones by the fungus Corynespora cassiicola CBS 161.60 results in a mechanistically unique intramolecular ring-D cyclization resulting in C-14 spiro-lactones

Metabolism of steroidal lactones by the fungus Corynespora cassiicola CBS 161.60 results in a mechanistically unique intramolecular ring-D cyclization resulting in C-14 spiro-lactones

Syntheses and medicinal chemistry of spiro heterocyclic steroids

Ligand‐Controlled Regiodivergence in Nickel‐Catalyzed Vinylcyclopropane Rearrangement

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