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Communication | Regular issue | Vol 83, No. 2, 2011, pp.293-298
Published online, 28th December, 2010
DOI: 10.3987/COM-10-12106
Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions

Hisashi Takada, Shinji Nagumo,* Eiko Yasui, Megumi Mizukami, and Masaaki Miyashita*

*Department of Applied Chemistry, Faculty of Engineering, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo, 192-0015, Japan


The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the α,β-unsaturated γ,δ-epoxy ester system and an epoxy alcohol derivative as the key steps.