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Total Synthesis of the Polyoxygenated Sesquiterpenes Guignarderemophilanes C and D


Ilazi, Agron; Liffert, Raphael; Gademann, Karl (2018). Total Synthesis of the Polyoxygenated Sesquiterpenes Guignarderemophilanes C and D. Helvetica Chimica Acta, (101):e1800011.

Abstract

The total syntheses of the neural anti‐inflammatory agents guignarderemophilanes C and D have been accomplished for the first time starting from γ‐hydroxy carvone in 15 and 14 steps, respectively. The presented synthetic route proceeds via a known intermediate, whose synthesis has been elaborated in our group in the course of the total synthesis of the sesquiterpenoid periconianone A. Key for the successful conversion of this intermediate into both targets was finding a suitable strategy to install the 1,2,3‐trihydroxylated A‐ring scaffold. For this purpose, we effectively employed a Mitsunobu inversion, epoxidation, and regioselective epoxide opening sequence, before the bicyclic ring system was constructed by an aldol condensation reaction on a sterically demanding substrate. Our reported synthesis set the stage for SAR studies to prepare even more potent compounds by modification and derivatization of the natural product's scaffold.

Abstract

The total syntheses of the neural anti‐inflammatory agents guignarderemophilanes C and D have been accomplished for the first time starting from γ‐hydroxy carvone in 15 and 14 steps, respectively. The presented synthetic route proceeds via a known intermediate, whose synthesis has been elaborated in our group in the course of the total synthesis of the sesquiterpenoid periconianone A. Key for the successful conversion of this intermediate into both targets was finding a suitable strategy to install the 1,2,3‐trihydroxylated A‐ring scaffold. For this purpose, we effectively employed a Mitsunobu inversion, epoxidation, and regioselective epoxide opening sequence, before the bicyclic ring system was constructed by an aldol condensation reaction on a sterically demanding substrate. Our reported synthesis set the stage for SAR studies to prepare even more potent compounds by modification and derivatization of the natural product's scaffold.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Language:English
Date:2018
Deposited On:03 Apr 2018 15:53
Last Modified:29 Jul 2020 07:07
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Additional Information:For accepted manuscripts: This is the peer reviewed version of the following article: Ilazi, Agron; Liffert, Raphael; Gademann, Karl (2018). Total Synthesis of the Polyoxygenated Sesquiterpenes Guignarderemophilanes C and D. Helvetica Chimica Acta, (101):e1800011., which has been published in final form at https://doi.org/10.1002/hlca.201800011. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
OA Status:Green
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/hlca.201800011
Project Information:
  • : FunderSNSF
  • : Grant ID200020_163151
  • : Project TitleDirecting Neurite Outgrowth through Synthetic Natural Products

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