A Stereoselective Photoinduced Cycloisomerization Inspired by Ophiobolin A

30 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A concise, modular, and stereoselective synthetic entry point to the 5-8-5 carbocyclic core of the ophiobolins is described. This strategy exploits the chiral tertiary alcohol of ophiobolin A to guide assmebly of the 5-8-5 scaffold in a single step via photoinitiated isomerization. Mechanistic insights into the origin of stereocontrol in this reaction are described, as are efforts to elaborate the resultant 5-8-5 polycycle to the pharmacophore of ophiobolin A.

Keywords

Synthesis
Photochemistry
Mechanism
Natural Products

Supplementary materials

Title
Description
Actions
Title
Supporting Information
Description
Detailed procedures, characterization data for organic compounds, and computational data.
Actions

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.