Abstract
A total synthesis of the neuritegenic agent, epolactaene has been achieved via a convergent approach in 14 steps from optically active lactaldehyde derivatives. The key steps include (i) the stereoselective aldol reaction between malonate ester enolate and α-alkoxy aldehyde (ii) diastereospecific lactonization of malonate ester (iii) E-selective Wittig reaction. The optical rotation was identical with that of the natural (+) -epolactaene, which establishes that the absolute configuration of natural (+) -epolactaene is (13R, 14R) definitively. Other several epoxy-γ-lactam compounds also synthesized which suggest this method would be general for organic synthesis.
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