Excel, ORD, and NMR spectroscopy files for: Total synthesis of Honokiol via oxidative phenol coupling
Data files
Sep 25, 2025 version files 16.05 MB
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FID_For_Publication.zip
15.83 MB
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README.md
4.24 KB
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Supporting_Information_(Excel).zip
197.82 KB
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Supporting_Information_(ORD).zip
21.68 KB
Abstract
Herein, we disclose the total synthesis of honokiol in six steps with an overall yield of 66%. Two distinct routes were explored, with the key steps being highly efficient and selective cross-couplings of commercially available phenols to construct the main biphenolic backbone. The routes employ inexpensive reagents and are scalable, high-yielding processes. The experimental procedures are reported in the conventional narrative format and in two machine-readable formats.
The "Supporting_Information_(ORD).zip" files (.pb and .pbtxt) can be uploaded directly to the ORD platform for visual analysis of reaction schemes. Alternatively, these files can be opened in a text editor like Notepad, which will display only the underlying code generated by ORD.
The "Supporting_Information_(Excel).zip" file includes an Excel spreadsheet modeled after the ORD platform, using similar methods for data entry. Each experiment from the Excel file has also been exported as an individual CSV file. See more details below.
The "FID_For_Publication.zip" file contains the raw spectroscopic data.
Description of the data and file structure
Excel Template
The Excel file is organized by individual reaction steps. “G1” and “G2” indicate the synthesis generation. The third digit represents the reaction step within the sequence, while the accompanying letter (A–C) specifies the protocol variant for that step. For example, the sheet labeled G2-2B corresponds to the second-generation synthesis, step two, using the second variant of the protocol.
To improve machine readability, dropdown menus were implemented to restrict inputs to fixed units.
- Dropdown menus are highlighted in red cells.
- The "Menu Options" sheet contains all the source data for the dropdown menus.
- When copying a cell with a dropdown menu, both the formatting and the dropdown functionality will be copied, not just the displayed value.
Color Coding: Aside from the red cells, the varying colors within a template are meant only to guide the user across different sections of the template. Cells with no color should be left blank.
The "README" sheet provides step-by-step instructions for adding options to a dropdown menu. A copy of the instructions from this README file is also included.
The "Analysis Table" sheet contains blank analysis templates. These can be copied and pasted into a new template depending on the type of analysis required for a given experiment.
Excel Template Sections
Chemicals: Only enough information to accurately identify each compound and the amount used is required. When non-common reagents are used, a SMILES string and/or CAS# should also be included. Rows may be added or removed as needed.
Conditions: Try to input as much information as possible. Do not delete unused rows. Instead, leave them blank.
Set up: Report procedures based on individual steps and assign each step accordingly. Rows may be added or removed as needed.
Isolation: When reporting flash chromatography conditions, include as much detail as possible. For isolations performed using other methods, describe each step of the procedure.
Analysis: Enter data as instructed. Do not delete input labels under "Spectroscopy" (1H NMR or 13 NMR). If using a General NMR template, complete the required fields and provide the NMR data as a single text string in the "NMR Data" field. For General Analysis, provide the data as a single text string in the "Data" field.
Leave unused cells blank; this helps keep the template organized and easy to navigate. Once completed, export the template as a CSV file.
A CSV file corresponding to each sheet in the Excel template has been provided. For users without access to Excel, a blank CSV template is included along with the necessary supporting files (menu options, analysis table, and a copy of this README file). Please note that in the CSV format, dropdown menu functionality and color coding are not retained; however, the overall structure and reporting remain the same.
Our Goal
Our overarching aim is not to debate formatting preferences, but to contribute to the broader discussion on improving data reproducibility. This submission is intended to illustrate potential approaches for achieving that goal. The data presented in these files are not meant to represent a flawless report, but rather to highlight how much information is typically omitted when protocols are submitted in a traditional paragraph-based format.