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Published July 30, 2021 | Accepted Version + Supplemental Material
Journal Article Open

Synthetic strategy toward ineleganolide: A cautionary tale


We present a case study to demonstrate how complex molecule synthesis can benefit from quantum mechanics (QM) calculations. Theory is applied in two contexts: testing the chemical intuition used in retrosynthetic planning, along with expediting the resolution of unexpected challenges encountered during the course of the synthesis. From a computational lens, we examine retrospectively the strategies employed and the decisions made during our synthetic efforts toward the diterpenoid natural product ineleganolide. Seemingly logical and robust hypotheses are found to be ill-fated after theoretical investigation. Prior knowledge of these issues may have potentially saved valuable time and resources during our synthetic efforts. This cautionary tale suggests that synthetic campaigns can benefit from computational evaluation of synthetic plans.

Additional Information

© 2021 Elsevier Ltd. Received 2 May 2021, Revised 10 June 2021, Accepted 10 June 2021, Available online 23 June 2021. We thank the NIH (R01 GM080269) and Caltech for financial support. The Caltech High Performance Computing (HPC) center is acknowledged for support of computational resources. This article is dedicated to Prof. Dale L. Boger. The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Attached Files

Accepted Version - nihms-1716969.pdf

Supplemental Material - ScienceDirect_files_26Jul2021_16-12-31.219.zip


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August 22, 2023
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