Evidence map›Paper›PMID 31693792›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Total Synthesis of (+)-6-epi-Ophiobolin A.

Danny Q Thach, Zachary G Brill, Huck K Grover, Kenneth V Esguerra, Jordan K Thompson, Thomas J Maimone

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing 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

19 citing papers in PubMed.

  1. Article
  2. Asymmetric Total Synthesis and Structure Revision of (+)-Mangicol D.Journal of the American Chemical Society · 2026
    Article
  3. Review
  4. Evolution of a Synthetic Strategy for Complex Diterpenes fromJournal of the American Chemical Society · 2026
    Article
  5. Review
  6. Article
  7. Article
  8. Article
  9. Review
  10. Article
  11. Article
  12. Synthesis of (-)-Cotylenol, a 14-3-3 Molecular Glue Component.Journal of the American Chemical Society · 2023
    Article
  13. Review
  14. Article
  15. Review
  16. Article
  17. The Biosynthesis and Transport of Ophiobolins inInternational journal of molecular sciences · 2022
    Article
  18. Article
  19. 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

6 authors.

Danny Q ThachDepartment of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.
Zachary G BrillDepartment of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.
Huck K GroverDepartment of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.
Kenneth V EsguerraDepartment of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.
Jordan K ThompsonDepartment of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.
Thomas J MaimoneDepartment of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA, 94720, USA.ORCID 0000-0001-5823-692X

Funding

Synthesis of Complex Terpenes From Simple Precursors: RenewalR01GM116952 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI MAIMONE, THOMAS JOHN · 2016 to 2024
$2.7M
A proposal for the purchase of a new Cu anode Microsource X-ray Diffractometer wiS10RR027172 · NCRR · UNIVERSITY OF CALIFORNIA BERKELEY · PI RAYMOND, KENNETH N · 2010 to 2010
$500k
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
Directorate for Education and Human Resources DGE-1106400NCRR NIH HHS S10 RR027172NIGMS NIH HHS R01 GM116952NIH HHS S10 OD024998
6 · The paper itself

Abstract

The ophiobolin sesterterpenes are notable plant pathogens which have recently elicited significant chemical and biological attention because of their intriguing carbogenic frameworks, reactive functionalities, and emerging anticancer profiles. Reported herein is a total synthesis of (+)-6-epi-ophiobolin A in 14 steps, a task which addresses construction of the synthetically challenging spirocyclic tetrahydrofuran motif as well as several other key stereochemical problems. This work demonstrates a streamlined synthetic platform to complex ophiobolins leveraging disparate termination modes of a radical polycyclization cascade for divergent elaboration and functionalization.

Indexed as

Biological ProductsSesterterpenesBiological Productsophiobolin ASesterterpenesnatural productsradical reactionsspirocyclesterpenestotal synthesis

Identifiers

PMID31693792
PMCPMC6980906

What OpenQuestion holds

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Registered trials

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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.