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Total synthesis of the sesquiterpenoid periconianone a based on a postulated biogenesis


Liffert, Raphael; Linden, Anthony; Gademann, Karl (2017). Total synthesis of the sesquiterpenoid periconianone a based on a postulated biogenesis. Journal of the American Chemical Society, 139(45):16096-16099.

Abstract

The first enantioselective total synthesis of the complex tricarbocyclic sesquiterpenoid periconianone A based on a postulated biogenesis is reported. Key elements of the synthetic route include the use of an isopropenyl group as a removable directing group for stereoselective synthesis, a sequence featuring a Rh-mediated O–H insertion/[3,3]-sigmatropic rearrangement and subsequent α-ketol rearrangement, and a late stage aldol reaction to furnish the complex cage-like framework.

Abstract

The first enantioselective total synthesis of the complex tricarbocyclic sesquiterpenoid periconianone A based on a postulated biogenesis is reported. Key elements of the synthetic route include the use of an isopropenyl group as a removable directing group for stereoselective synthesis, a sequence featuring a Rh-mediated O–H insertion/[3,3]-sigmatropic rearrangement and subsequent α-ketol rearrangement, and a late stage aldol reaction to furnish the complex cage-like framework.

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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
Language:English
Date:2017
Deposited On:18 Jan 2018 17:17
Last Modified:19 Aug 2018 12:50
Publisher:American Chemical Society (ACS)
ISSN:0002-7863
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/jacs.7b10053
PubMed ID:29076340
Project Information:
  • : FunderSNSF
  • : Grant ID200020_163151
  • : Project TitleDirecting Neurite Outgrowth through Synthetic Natural Products

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