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Efficient Solid-Phase Synthesis of Clavulones via Sequential Coupling of α- and ω-Chains

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journal contribution
posted on 01.04.2004, 00:00 authored by Hiroshi Tanaka, Tsuyoshi Hasegawa, Makoto Iwashima, Kazuo Iguchi, Takashi Takahashi
We describe an efficient solid-phase synthesis of clavulones via the sequential coupling of the α- and ω-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 α-chain.