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Synthesis of 3-epi-Hypatulin B Featuring a Late-Stage Photo-Oxidation in Flow

28 February 2022, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

A total synthesis of 3-epi-hypatulin B, a highly oxygenated and densely functionalized bicyclic scaffold, is reported. The carbon skeleton was prepared by functionalization of a cyclopentanone core and an intramolecular Mukaiyama aldol reaction. The synthesis features a late-stage photo-oxidation of a methoxyallene intermediate for the installation of an ester functionality. Problems encountered during the batch process were solved by translation of the transformation into a flow protocol. Our synthesis highlights the value of flow chemistry to enable challenging steps in natural product synthesis.

Keywords

Total Synthesis
Natural Products
Flow Chemistry

Supplementary materials

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Supporting Information
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Synthetic Procedures, Spectra, HPLC, X-ray
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Now Published

Synthesis of 3-epi-Hypatulin B Featuring a Late-Stage Photo-Oxidation in Flow [opens in a new tab]
Stefan Leisering, Sebastian Ponath, Kamar Shakeri, Alexandros Mavroskoufis, Merlin Kleoff, Patrick Voßnacker, Simon Steinhauer, Manuela Weber, Mathias Christmann journal article
Organic Letters , Volume 24, Issue 24
Online publication date: May 10, 2022

Version History

Feb 28, 2022 Version 1

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

DOI

10.26434/chemrxiv-2022-jjkk3
D O I: 10.26434/chemrxiv-2022-jjkk3 [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) have declared ethics committee/IRB approval is not relevant to this content

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