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Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids

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Macabeo, Allan Patrick ; Kreuzer, Andreas ; Reiser, Oliver
License: Allianz- bzw. Nationallizenz
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Date of publication of this fulltext: 25 Jul 2016 10:38


Titanium chelate addition of aryl nucleophiles to cyclopropyl aldehyde 6 followed by a tin-catalyzed one-pot retro-aldol, acetalisation and lactonisation sequence afforded cis and trans γ-aryllactone acetals. A γ-furyllactone derived by this approach was further transformed in two steps to model compounds for the oxidised northeastern sectors of selected Pseudopterogorgia diterpenoids.

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