Cambridge Open Engage home
What is Cambridge Open Engage?
How to Submit
Browse
About
News [opens in a new tab]

A Bio-Inspired Synthesis of Peshawaraquinone

08 August 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A ten-step bio-inspired enantioselective synthesis of peshawaraquinone, an uncommon and complex naphthoquinone mero-terpenoid is described. Key to the success of this synthetic pathway is a well-tuned HFIP-promoted metal-free allylation was developed to coupling lawsone with allylic alcohols, together with an usual organo-catalyzed [3+2] cycloaddition for con-structing the bicyclo[3.2.1]octane core structure. Further investigation disclosed peshawaraquione is a racemic mixture.

Keywords

total synthesis
biomimetic synthesis

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.

Version History

Aug 08, 2022 Version 1

Metrics

962
541
4
Views
Downloads

License

CC logo
CC
BY logo
BY
NC logo
NC
ND logo
ND
The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-drjln
D O I: 10.26434/chemrxiv-2022-drjln [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

Share