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Retrosynthetic strategies and their impact on synthesis of arcutane natural products

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Abstract

Retrosynthetic analysis is a cornerstone of modern natural product synthesis, providing an array of tools for disconnecting structures. However, discussion of retrosynthesis is often limited to the reactions used to form selected bonds in the forward synthesis. This review details three strategies for retrosynthesis, focusing on how they can be combined to plan the synthesis of polycyclic natural products, such as atropurpuran and the related arcutane alkaloids. Recent syntheses of natural products containing the arcutane framework showcase how these strategies for retrosynthesis can be combined to plan the total synthesis of highly caged scaffolds. Comparison of multiple syntheses of the same target provides a unique opportunity for detailed analysis of the impact of retrosynthetic disconnections on synthesis outcomes.

Graphical abstract: Retrosynthetic strategies and their impact on synthesis of arcutane natural products

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Article information


Submitted
10 Mar 2020
Accepted
20 Apr 2020
First published
21 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Minireview

Retrosynthetic strategies and their impact on synthesis of arcutane natural products

S. V. McCowen, N. A. Doering and R. Sarpong, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC01441A

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