Cyclic Allyl Carbamates in Stereoselectivesyn SE′ 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 C1,C10 cis-disubstituted cyclohexene derivative is obtained in 86 % yield with total stereoselectivity. The reaction is based on a syn...

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Bibliographic Details
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 Wiley-VCH Verlag 2007
Subjects
Chemical Sciences
Medicinal Chemistry
Organic chemistry
syn SE
Synthesis
Terpenoids
Carbamates
Cytotoxic agents
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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 C1,C10 cis-disubstituted cyclohexene derivative is obtained in 86 % yield with total stereoselectivity. The reaction is based on a syn SE′ process involving a cyclic (Z)-allyl diisopropylcarbamate.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700490