Evidence map›Paper›PMID 31808282›Full record

ReviewAngewandte Chemie (International ed. in English)2020

A Case for Bond-Network Analysis in the Synthesis of Bridged Polycyclic Complex Molecules: Hetidine and Hetisine Diterpenoid Alkaloids.

Nicolle A Doering, Richmond Sarpong, Reinhard W Hoffmann

Abstract readReview
In one paragraph

Review 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 12 papers.

0numbers the graph read from it
0cells of the map it votes in
12citing 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

12 citing papers in PubMed.

  1. Review
  2. Article
  3. Article
  4. Azine Dearomatization in Natural Product Total Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Review
  5. Article
  6. Navigating Excess Complexity: Total Synthesis of Daphenylline.Journal of the American Chemical Society · 2024
    Article
  7. Review
  8. Review
  9. Article
  10. Article
  11. Review
  12. 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

3 authors.

Nicolle A DoeringLatimer Hall, Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.ORCID 0000-0001-5191-2120
Richmond SarpongLatimer Hall, Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.ORCID 0000-0002-0028-6323
Reinhard W HoffmannFachbereich Chemie der Philipps Universität Marburg, 35032, Marburg, Germany.ORCID 0000-0001-6680-849X

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A key challenge in the synthesis of diterpenoid alkaloids lies in identifying strategies that rapidly construct their multiply bridged polycyclic skeletons. Existing approaches to these structurally intricate secondary metabolites are discussed in the context of a "bond-network analysis" of molecular frameworks, which was originally devised by Corey some 40 years ago. The retrosynthesis plans that emerge from a topological analysis of the highly bridged frameworks of the diterpenoid alkaloids are discussed in the context of eight recent syntheses of hetidine and hetisine natural products and their derivatives. This Minireview highlights the extent to which network analyses of the type described here sufficed for designing synthesis plans, as well as areas where they had to be amalgamated with functional group oriented synthetic planning considerations.

Indexed as

AlkaloidsDiterpenesHydrocarbons, CyclicHydrogen BondingMolecular StructureAlkaloidsDiterpenesHydrocarbons, Cyclicalkaloidspolycyclessynthesis designterpenoidstotal synthesis

Identifiers

PMID31808282
PMCPMC7317470

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.