Title of article
Sulfanyl Radical-Induced Cyclization of Linalyl Acetate to the Iridane Skeleton: A Short Synthesis of (±)Dehydroiridomyrmecin
Author/Authors
Barrero، Alejandro F. نويسنده , , Arseniyadis، Simeon نويسنده , , Moral، Jose F. Quilez del نويسنده , , Herrador، M. Mar نويسنده , , Arteaga، Jes?s F. نويسنده , , Sanchez، Elena M. نويسنده ,
Issue Information
روزنامه با شماره پیاپی سال 2005
Pages
-590
From page
591
To page
0
Abstract
Sulfanyl radicals promote radical cyclization both in linalyl acetate (2) and its derivative 3, leading highly selectively to monoterpenoids with an iridane skeleton. We have investigated the addition of different sulfanyl radicals such as PhS•, 4NO2C6H4S• and PhCH2CH2S• and found that the latter radical produces the best results (87-93%). Natural iridoid dehydroiridomyrmecin (1) at an overall yield of 28% was synthesized in four steps using this method.
Keywords
addition-cyclization reaction , iridane skeleton , sulfanyl radical , dehydroiridomyrmecin , polyprenes
Journal title
Synlett
Serial Year
2005
Journal title
Synlett
Record number
110605
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