Evidence map›Paper›PMID 38032339›Full record

ArticleAngewandte Chemie (International ed. in English)2024

Unified Synthesis of 2-Isocyanoallopupukeanane and 9-Isocyanopupukeanane through a "Contra-biosynthetic" Rearrangement.

Melissa A Hardy, Jack Hayward Cooke, Zhitao Feng, Kenta Noda, Isabel Kerschgens, Lynée A Massey, Dean J Tantillo, Richmond Sarpong

Erratum issuedAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Review
  2. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

8 authors.

Melissa A HardyDepartment of Chemistry, University of California, Berkeley, CA 94720, USA.ORCID https://orcid.org/0000-0002-3924-4518
Jack Hayward CookeDepartment of Chemistry, University of California, Berkeley, CA 94720, USA.ORCID https://orcid.org/0000-0002-9810-0610
Zhitao FengDepartment of Chemistry, University of California, Davis, CA 95616, USA.
Kenta NodaDepartment of Chemistry, University of California, Berkeley, CA 94720, USA.
Isabel KerschgensDepartment of Chemistry, University of California, Berkeley, CA 94720, USA.
Lynée A MasseyDepartment of Chemistry, University of California, Berkeley, CA 94720, USA.
Dean J TantilloDepartment of Chemistry, University of California, Davis, CA 95616, USA.ORCID https://orcid.org/0000-0002-2992-8844
Richmond SarpongDepartment of Chemistry, University of California, Berkeley, CA 94720, USA.ORCID https://orcid.org/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 OD024998NIH HHS S10OD024998
6 · The paper itself

Abstract

Herein, we describe our synthetic efforts toward the pupukeanane natural products, in which we have completed the first enantiospecific route to 2-isocyanoallopupukeanane in 10 steps (formal synthesis), enabled by a key Pd-mediated cyclization cascade. This subsequently facilitated an unprecedented bio-inspired "contra-biosynthetic" rearrangement, providing divergent access to 9-isocyanopupukeanane in 15 steps (formal synthesis). Computational studies provide insight into the nature of this rearrangement.

Indexed as

Carbocation RearrangementChiral PoolCyclization CascadeNatural Product SynthesisSesquiterpenes

Identifiers

PMID38032339
PMCPMC11646677

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.