Biomimetic Total Synthesis of (±)-Lappaceolides A and B

Rajanish R. Pallerla; Jenna Hakola; Leevi Härkönen; Juha H. Siitonen

doi:10.1021/acs.orglett.5c02445

Biomimetic Total Synthesis of (±)-Lappaceolides A and B

Rajanish R. Pallerla
, Jenna Hakola
, Leevi Härkönen
, Juha H. Siitonen^*

^*Corresponding author for this work

Aalto University

Research output: Contribution to journal › Article › Scientific › peer-review

1 Citation (Scopus)

8 Downloads (Pure)

Abstract

The first total synthesis of lappaceolides A and B is achieved in two steps by using a biomimetic vinylogous-Michael–oxa-Michael domino reaction. The domino reaction proceeds with Cs₂CO₃in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof of the biosynthetic hypothesis of lappaceolides being dimers of the natural product siphonodin.

Original language	English
Pages (from-to)	11149-11151
Number of pages	3
Journal	Organic Letters
Volume	27
Issue number	40
Early online date	1 Oct 2025
DOIs	https://doi.org/10.1021/acs.orglett.5c02445
Publication status	Published - 10 Oct 2025
MoE publication type	A1 Journal article-refereed

Funding

J.H.S. acknowledges funding from Aalto University and FinnCERES.

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10.1021/acs.orglett.5c02445Licence: CC BY

Biomimetic_Total_Synthesis_of_Lappaceolides_A_and_BFinal published version, 1.14 MBLicence: CC BY

Cite this

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title = "Biomimetic Total Synthesis of (±)-Lappaceolides A and B",

abstract = "The first total synthesis of lappaceolides A and B is achieved in two steps by using a biomimetic vinylogous-Michael–oxa-Michael domino reaction. The domino reaction proceeds with Cs2CO3in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof of the biosynthetic hypothesis of lappaceolides being dimers of the natural product siphonodin.",

author = "Pallerla, \{Rajanish R.\} and Jenna Hakola and Leevi H{\"a}rk{\"o}nen and Siitonen, \{Juha H.\}",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society",

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doi = "10.1021/acs.orglett.5c02445",

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AU - Pallerla, Rajanish R.

AU - Hakola, Jenna

AU - Härkönen, Leevi

AU - Siitonen, Juha H.

PY - 2025/10/10

Y1 - 2025/10/10

N2 - The first total synthesis of lappaceolides A and B is achieved in two steps by using a biomimetic vinylogous-Michael–oxa-Michael domino reaction. The domino reaction proceeds with Cs2CO3in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof of the biosynthetic hypothesis of lappaceolides being dimers of the natural product siphonodin.

AB - The first total synthesis of lappaceolides A and B is achieved in two steps by using a biomimetic vinylogous-Michael–oxa-Michael domino reaction. The domino reaction proceeds with Cs2CO3in 1,2-DCE at elevated temperatures and requires careful kinetic control. The total synthesis provides further proof of the biosynthetic hypothesis of lappaceolides being dimers of the natural product siphonodin.

UR - https://www.scopus.com/pages/publications/105018344681

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DO - 10.1021/acs.orglett.5c02445

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SP - 11149

EP - 11151

JO - Organic Letters

JF - Organic Letters

IS - 40

ER -

Biomimetic Total Synthesis of (±)-Lappaceolides A and B

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CCDC 2387316: Experimental Crystal Structure Determination

-: FinnCERES

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Biomimetic Total Synthesis of (±)-Lappaceolides A and B

Abstract

Funding

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CCDC 2387316: Experimental Crystal Structure Determination

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-: FinnCERES

Cite this