Evidence map›Paper›PMID 39481083›Full record

ArticleJournal of the American Chemical Society2024

Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers.

Samantha R Angle, Hayden A Sharma, Christie K Choi, Kathryn E Carlson, Yingwei Hou, Jerome C Nwachukwu, Sung Hoon Kim, Benita S Katzenellenbogen, Kendall W Nettles, John A Katzenellenbogen and 1 more

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Article
  3. 1,2-Migratory ring expansion of a BN-naphthalene.Organic & biomolecular chemistry · 2025
    Article
  4. Article
  5. Article
  6. Review
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

11 authors.

Samantha R AngleDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.ORCID 0009-0009-9769-4806
Hayden A SharmaDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
Christie K ChoiDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.ORCID 0009-0002-4005-5367
Kathryn E CarlsonDepartment of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Yingwei HouDepartment of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Jerome C NwachukwuDepartment of Immunology and Microbiology, The Wertheim UF Scripps Institute for Biomedical Innovation and Technology, Jupiter, Florida 33458, United States.
Sung Hoon KimDepartment of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Benita S KatzenellenbogenDepartment of Molecular and Integrative Physiology and Cancer Center, University of Illinois, Urbana, Illinois 61801, United States.ORCID 0000-0002-8847-2752
Kendall W NettlesDepartment of Immunology and Microbiology, The Wertheim UF Scripps Institute for Biomedical Innovation and Technology, Jupiter, Florida 33458, United States.
John A KatzenellenbogenDepartment of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.ORCID 0000-0003-0914-0010
Eric N JacobsenDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.ORCID 0000-0001-7952-3661

Funding

CHIRAL COMPLEXES DESIGNED TO CATALYZE ORGANIC REACTIONSR01GM043214 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI JACOBSEN, ERIC N · 1991 to 2023
$9.4M
Chiral Catalysts Designed to Catalyze Organic ReactionsR37GM043214 · NIGMS · HARVARD UNIVERSITY · PI JACOBSEN, ERIC N · 2002 to 2011
$6.6M
Development, Elucidation, and Application of New Principles in Stereoselective CatalysisR35GM149244 · NIGMS · HARVARD UNIVERSITY · PI ERIC N JACOBSEN · 2023 to 2026
$3.2M
Chemical, structural and molecular rules for fully antagonizing the estrogen receptorR01CA220284 · NCI · UNIVERSITY OF FLORIDA · PI KATZENELLENBOGEN, BENITA S, KATZENELLENBOGEN, JOHN A. · 2018 to 2022
$2.8M
Mechanisms of estrogen receptor ligand signalingR01CA275142 · NCI · UNIVERSITY OF FLORIDA · PI Kendall W Nettles · 2023 to 2026
$1.9M
NCI NIH HHS R01 CA220284NCI NIH HHS R01 CA275142NIGMS NIH HHS R01 GM043214NIGMS NIH HHS R35 GM149244NIGMS NIH HHS R37 GM043214
6 · The paper itself

Abstract

We report the development of an iterative Matteson homologation reaction with catalyst-controlled diastereoselectivity through the design of a new catalyst. This reaction was applied to the selective synthesis of each stereoisomer of benzestrol, a bioactive compound with estrogenic activity featuring three contiguous stereocenters. The different stereoisomers were assayed to determine their binding affinity for the estrogen receptor α (ERα), and the absolute configuration of the compound having uniquely high activity was determined. This research lays a framework for the catalytic synthesis and study of complete stereoisomeric sets of other bioactive molecules and chemical probes containing contiguous stereocenters.

Indexed as

Estrogen Receptor alphaCatalysisHumansMolecular StructureStereoisomerismEstrogen Receptor alpha

Identifiers

PMID39481083
PMCPMC11836471

What Socratic holds

Textmetadata
LicenceTDM
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.