Curate this paper into an ORD dataset

Build an Open Reaction Database (ORD) dataset of the reactions reported in:

• Paper: High-Throughput Approach toward the Development of a Mizoroki–Heck Reaction To Access Tricyclic Spirolactones
• Authors: James R. Annand, Paul S. Riehl, Danielle M. Schultz et al.
• Published: JOC, 2020-06-16
• DOI: 10.1021/acs.joc.0c00997
• ORD wishlist card: open on GitHub

The reference input card holds these facts, the source-data locations and the notes below in machine-readable form.

Scope

Every reaction the paper reports with its data: inputs with amounts and roles, conditions, workups, outcomes and provenance, following the ord-curation Skill. Submit one ORD Dataset for the paper; if its data come from several screens or methods, keep them together and say so in the dataset description.

Source data

J. Org. Chem. 2020, 85, 9071-9079 (DOI 10.1021/acs.joc.0c00997). Microscale high-throughput experiments were used to find and optimise an intramolecular Mizoroki-Heck reaction that builds the tricyclic spirolactone core of the ent-kaurene diterpenes. The HTE dataset tables are in the Supporting Information PDF, which ACS normally provides free. The article itself is closed access. No machine-readable data file or SMILES is known, so substrate and product structures must be drawn from the scheme figures and converted to SMILES. The size of the screen has not been confirmed.

Known locations:

• https://pubs.acs.org/doi/10.1021/acs.joc.0c00997: J. Org. Chem. 2020, 85, 9071-9079 article and Supporting Information (HTE dataset tables per the ORD board notes) (license: ACS publisher copyright (article closed access; Crossref lists STM text-and-data-mining policy URLs only))
• https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=DOI:%2210.1021/acs.joc.0c00997%22&format=json: Europe PMC record (PMID 32539398). Not in PMC and no free full text. (license: n/a (metadata))

Pitfalls

The complex polycyclic substrate and spirolactone product need careful stereochemistry in SMILES. Screening yields may be HPLC or assay yields against an internal standard rather than isolated yields, so the analysis type must be recorded correctly. Microscale plate conditions (catalyst and ligand loadings, bases, solvents) must be mapped per well from the SI tables.

Deliver

• dataset: the ORD Dataset, compressed (.binpb.gz, .pb.gz, .txtpb.gz, .pbtxt.gz or .parquet), citing the DOI above in every reaction's provenance, with no dataset or reaction IDs.
• sources: a .zip with a README.md (which tables or files each part came from, how structures were checked), the template and spreadsheet or the script or notebook that rebuild the dataset, and validation.txt, the output of ORD's validator (ord-schema 0.8.3) on the dataset file.

Before you start

Open the wishlist card. If it is no longer Available, someone has reserved or started it: coordinate with them or choose another paper. Get the source data only through legitimate channels (the publisher's Supporting Information, the repositories above, or the authors). Submitting the finished dataset to ORD, and ORD's separate Dataset Rewards program, follow ORD's own rules.