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Biomimetic Total Synthesis of Lappaceolides A and B

17 July 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A two-step total synthesis of lappaceolides A and B is achieved using a biomimetic vinylogous-Michael–oxa-Michael domino reaction. The domino reaction proceeds with Cs2CO3 in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof to the biosynthetic hypothesis of lappaceolides as being dimers of the natural product siphonodin.

Keywords

Total synthesis
Biomimetic synthesis
Domino reaction

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Version History

Jul 17, 2024 Version 1

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

DOI

10.26434/chemrxiv-2024-v338f
D O I: 10.26434/chemrxiv-2024-v338f [opens in a new tab]

Funding

Academy of Finland
354458
FinnCERES
Aalto University

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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