Cyclic allyl carbamates in stereoselective syn SE′ processes: Synthetic approach to sarcodictyins and eleutherobin

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Abstract

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 S E′ process involving a cyclic (Z)-allyl diisopropylcarbamate. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Dhulut, S., Bourin, A., Lannou, M. I., Fleury, E., Lensen, N., Chelain, E., … Fahy, J. (2007). Cyclic allyl carbamates in stereoselective syn SE′ processes: Synthetic approach to sarcodictyins and eleutherobin. European Journal of Organic Chemistry, (31), 5235–5243. https://doi.org/10.1002/ejoc.200700490

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