Evidence map›Paper›PMID 32953008›Full record

ArticleChemical science2020

A unified strategy to reverse-prenylated indole alkaloids: total syntheses of preparaherquamide, premalbrancheamide, and (+)-VM-55599.

Jose B Roque, Eduardo V Mercado-Marin, Sven C Richter, Danilo Pereira de Sant'Ana, Ken Mukai, Yingda Ye, Richmond Sarpong

Abstract read
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In one paragraph

Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025
    Article
  2. Enantioselective Spirocyclization of Pd-Enolates and Isocyanates.Angewandte Chemie (International ed. in English) · 2025
    Article
  3. Review
  4. 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

7 authors.

Jose B RoqueDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.ORCID 0000-0002-5449-1584
Eduardo V Mercado-MarinDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.
Sven C RichterDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.
Danilo Pereira de Sant'AnaDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.
Ken MukaiDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.
Yingda YeDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.
Richmond SarpongDepartment of Chemistry , University of California , Berkeley , California 94720 , USA . Email: rsarpong@berkeley.edu.ORCID 0000-0002-0028-6323

Funding

Strategies and Methods for Complex Molecule Synthesis: Acquisition of a 400 MHz Nuclear Magnetic Resonance Spectrometer ConsoleR35GM130345 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI Richmond Sarpong · 2019 to 2026
$5.4M
Acquisition of a Cryoprobe and Related Accessories for a 600 MHz NMR Spectrometer to Support Health Research Activities at the University of California, BerkeleyS10OD024998 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI HARTWIG, JOHN F · 2018 to 2018
$265k
NIGMS NIH HHS R35 GM130345NIH HHS S10 OD024998
6 · The paper itself

Abstract

A full account of our studies toward reverse-prenylated indole alkaloids that contain a bicyclo[2.2.2]core is described. A divergent route is reported which has resulted in the synthesis of preparaherquamide, (+)-VM-55599, and premalbrancheamide. An intramolecular Dieckmann cyclization between an enolate and isocyanate was used to forge the bicyclo[2.2.2]diazaoctane core that is characteristic of these molecules. The pentacyclic indole scaffold was constructed through a one-pot Hofmann rearrangement followed by Fischer indole synthesis. The utilization of our previously reported indole peripheral functionalization strategy also led to natural products including malbrancheamides B, C, stephacidin A, notoamides F, I and R, aspergamide B, and waikialoid A. Ultimately, the divergent route that we devised provided access to a wide range of prenylated indole alkaloids that are differently substituted on the cyclic amine core.

Identifiers

PMID32953008
PMCPMC7480500

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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 OpenQuestion graph.