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Synthetic strategy toward ineleganolide: A cautionary tale

Cusumano, Alexander Q. and Houk, K. N. and Stoltz, Brian M. (2021) Synthetic strategy toward ineleganolide: A cautionary tale. Tetrahedron, 93 . Art. No. 132289. ISSN 0040-4020. PMCID PMC8294177. doi:10.1016/j.tet.2021.132289. https://resolver.caltech.edu/CaltechAUTHORS:20210629-212235037

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/j.tet.2021.132289DOIArticle
ORCID:
AuthorORCID
Cusumano, Alexander Q.0000-0002-2914-2008
Houk, K. N.0000-0002-8387-5261
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHR01 GM080269
CaltechUNSPECIFIED
Subject Keywords:Synthesis; Computational chemistry; Ineleganolide; QM calculations
PubMed Central ID:PMC8294177
DOI:10.1016/j.tet.2021.132289
Record Number:CaltechAUTHORS:20210629-212235037
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210629-212235037
Official Citation:Alexander Q. Cusumano, K.N. Houk, Brian M. Stoltz, Synthetic strategy toward ineleganolide: A cautionary tale, Tetrahedron, Volume 93, 2021, 132289, ISSN 0040-4020, https://doi.org/10.1016/j.tet.2021.132289.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:109658
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:29 Jun 2021 22:25
Last Modified:26 Jul 2021 22:28

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