Issue 29, 2020

Retrosynthetic strategies and their impact on synthesis of arcutane natural products

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

Article information

Article type
Minireview
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
Creative Commons BY-NC license

Chem. Sci., 2020,11, 7538-7552

Retrosynthetic strategies and their impact on synthesis of arcutane natural products

S. V. McCowen, N. A. Doering and R. Sarpong, Chem. Sci., 2020, 11, 7538 DOI: 10.1039/D0SC01441A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements