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Keywords = 5-epi-isospongiaquinone

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13 pages, 2921 KiB  
Article
General Methodologies Toward cis-Fused Quinone Sesquiterpenoids. Enantiospecific Synthesis of the epi-Ilimaquinone Core Featuring Sc-Catalyzed Ring Expansion
by Hilan Z. Kaplan, Victor L. Rendina and Jason S. Kingsbury
Molecules 2017, 22(7), 1041; https://doi.org/10.3390/molecules22071041 - 24 Jun 2017
Cited by 6 | Viewed by 6591
Abstract
A stereocontrolled approach to the cis-decalin framework of clerodane diterpenes and biologically active quinone sesquiterpenes is reported. Starting from an inexpensive optically pure tetrahydroindanone, Birch reductive alkylation builds two new contiguous chiral centers—one of which is quaternary and all-carbon-substituted. Also featured is [...] Read more.
A stereocontrolled approach to the cis-decalin framework of clerodane diterpenes and biologically active quinone sesquiterpenes is reported. Starting from an inexpensive optically pure tetrahydroindanone, Birch reductive alkylation builds two new contiguous chiral centers—one of which is quaternary and all-carbon-substituted. Also featured is a highly regioselective diazoalkane—carbonyl homologation reaction to prepare the 6,6-bicyclic skeleton. Therein, the utility of Sc(OTf)3 as a mild catalyst for formal 1C insertion in complex settings is demonstrated. Full article
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
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