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Efficient solid-phase synthesis of clavulones via sequential coupling of alpha- and omega-chains
Hiroshi Tanaka1, Tsuyoshi Hasegawa, Makoto Iwashima
1Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan.
Organic Letters
|March 26, 2004
Abstract:
We describe an efficient solid-phase synthesis of clavulones via the sequential coupling of the alpha- and omega-chains, involving two separate carbon-carbon bond-forming steps. The tetrahydropyranyl linker survived these reaction conditions and was cleaved without decomposing the unstable cross-conjugated dienones. Our methodology has allowed us to prepare six clavulone derivatives that are varied within the alpha-chain.