Header

UZH-Logo

Maintenance Infos

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids


Lardon, Nicolas; Liffert, Raphael; Linden, Anthony; Gademann, Karl (2019). The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids. Angewandte Chemie Internationale Edition, 58(21):7004-7007.

Abstract

Based on the structural similarities of the recently isolated eremophilane‐type sesquiterpenoids microsphaeropsisin B and C and the iso‐eremophilane periconianone C, a revised biogenetic hypothesis for C8–C11‐connected iso‐eremophilanes is presented and corroborated by strong experimental evidence. The first enantioselective total syntheses of microsphaeropsisin B and C were achieved starting from a known intermediate, whose synthesis was elaborated previously in the total synthesis of periconianone A, and in a total of 15 steps starting from γ‐hydroxy carvone. Mild reaction conditions for the subsequent α‐ketol rearrangement not only resulted in the herein proposed conversion of microsphaeropsisin B into periconianone C, but also in the conversion of microsphaeropsisin C into 4‐epi‐periconianone C.

Abstract

Based on the structural similarities of the recently isolated eremophilane‐type sesquiterpenoids microsphaeropsisin B and C and the iso‐eremophilane periconianone C, a revised biogenetic hypothesis for C8–C11‐connected iso‐eremophilanes is presented and corroborated by strong experimental evidence. The first enantioselective total syntheses of microsphaeropsisin B and C were achieved starting from a known intermediate, whose synthesis was elaborated previously in the total synthesis of periconianone A, and in a total of 15 steps starting from γ‐hydroxy carvone. Mild reaction conditions for the subsequent α‐ketol rearrangement not only resulted in the herein proposed conversion of microsphaeropsisin B into periconianone C, but also in the conversion of microsphaeropsisin C into 4‐epi‐periconianone C.

Statistics

Citations

Dimensions.ai Metrics
1 citation in Web of Science®
1 citation in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 31 Oct 2019
1 download since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis
Language:English
Date:20 May 2019
Deposited On:31 Oct 2019 14:27
Last Modified:01 Nov 2019 08:36
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/anie.201901898
Project Information:
  • : FunderSNSF
  • : Grant ID200020_163151
  • : Project TitleDirecting Neurite Outgrowth through Synthetic Natural Products

Download

Closed Access: Download allowed only for UZH members