Concise Synthesis of Naphthalene-Based 14-Aza-12-Oxasteroids.

Smriti Srivastava, Jun Luo, Daniel Whalen, Katherine N Robertson, Amitabh Jha

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

0 citing papers in PubMed.

No citing paper in PubMed yet.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors.

Smriti SrivastavaDepartment of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.ORCID 0000-0002-4405-4735

Jun LuoDepartment of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.

Daniel WhalenDepartment of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.

Katherine N RobertsonDepartment of Chemistry, Saint Mary's University, Halifax, NS B3H C3C, Canada.ORCID 0000-0002-5602-8059

Amitabh JhaDepartment of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.ORCID 0000-0002-6305-0721

Funding

Beatrice Hunter Cancer InstituteNatural Sciences and Engineering Research Council

6 · The paper itself

Abstract

A concise, transition metal-free four-step synthetic pathway has been developed for the synthesis of tetracyclic heterosteroidal compounds, 14-aza-12-oxasteroids, starting from readily available 2-naphthol analogues. After conversion of 2-naphthols to 2-naphthylamines by the Bucherer reaction, subsequent selective C-acetylation was achieved via the Sugasawa reaction and reduction of the acetyl group using borohydride, which resulted into the corresponding amino-alcohols. The naphthalene-based amino-alcohols underwent double dehydrations and double intramolecular cyclization with oxo-acids leading to one-pot formation of a C-N bond, a C-O bond and an amide bond in tandem, to generate two additional rings completing the steroidal framework. A series of 14-aza-12-oxasteroids were synthesized using our developed synthetic strategy in moderate yields, and the structure of one of the final products, 12a-Methyl-11-phenyl-11,12a-dihydro-1

Indexed as

14-aza-12-oxosteroidDean–Stark condensationdouble dehydrationheterosteroidsSugasawa reaction

Identifiers

PMID39860282

DOI10.3390/molecules30020415

PMCPMC11767449

What Socratic holds

Textmetadata

LicenceCC BY

Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.