Cyclic allyl Carbamates in stereoselective syn S-E' processes: Synthetic approach to sarcodictyins and eleutherobin

Our synthetic approach of marine diterpenoids sarcodictyins A and B and eleutherobin relies on the one-step attachment of a C5-C9 side chain at the C10 position. The Cl,C10 cisdisubstituted cyclohexene derivative is obtained in 86% yield with total stereoselectivity. The reaction is based on a syn S...

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Published inEuropean journal of organic chemistry Vol. 2007; no. 31; pp. 5235 - 5243
Main Authors Dhulut, Sylvie, Bourin, Arnaud, Lannou, Marie-Isabelle, Fleury, Etienne, Lensen, Nathalie, Chelain, Evelyne, Pancrazi, Ange, Ardisson, Janick, Fahy, Jacques
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.11.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
synthesis
terpenoids
DIELS-ALDER REACTIONS
CONVERGENT APPROACH
carbamates
ENANTIOSELECTIVE LITHIATION
SECONDARY ALLYLTITANIUM(IV) REAGENTS
GAMMA-DEPROTONATION
HOMOALDOL REACTION
ABSOLUTE-CONFIGURATION
HOMOENOLATE REAGENTS
syn S-E
METALATED NITROGEN DERIVATIVES
cytotoxic agents
ERYTHROPODIUM-CARIBAEORUM
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Summary:Our synthetic approach of marine diterpenoids sarcodictyins A and B and eleutherobin relies on the one-step attachment of a C5-C9 side chain at the C10 position. The Cl,C10 cisdisubstituted cyclohexene derivative is obtained in 86% yield with total stereoselectivity. The reaction is based on a syn S-E(') process involving a cyclic (Z)-allyl diisopropylearbamate. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700490