Non-natural Elemane as the “Stepping Stone” for the Synthesis of Germacrane and Guaiane Sesquiterpenes

The synthesis of hydroxyelemane 5 from (R)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction t...

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Veröffentlicht in:	Organic letters 2013-01, Vol.15 (1), p.152-155
Hauptverfasser:	Anagnostaki, Elissavet E, Zografos, Alexandros L
Format:	Artikel
Sprache:	eng
Schlagworte:	Cyclization Molecular Structure Monoterpenes - chemistry Sesquiterpenes, Guaiane - chemical synthesis Sesquiterpenes, Guaiane - chemistry Stereoisomerism
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creator	Anagnostaki, Elissavet E Zografos, Alexandros L
description	The synthesis of hydroxyelemane 5 from (R)-carvone and its utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction to access the 10-membered macrocyclic core of germacranes and the condensed 5–7 carbocycles of guaiane sesquiterpenes. Additionally, reactions of furanoguaianes under acidic or oxidizing reagents have been investigated, and preliminary results of these conversions are presented.
doi_str_mv	10.1021/ol3031999
format	Article
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subjects	Cyclization Molecular Structure Monoterpenes - chemistry Sesquiterpenes, Guaiane - chemical synthesis Sesquiterpenes, Guaiane - chemistry Stereoisomerism
title	Non-natural Elemane as the “Stepping Stone” for the Synthesis of Germacrane and Guaiane Sesquiterpenes
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