Tetrahedron Letters

Synthesis of lepiochlorin, an antibiotic metabolite of a fungus cultivated by ants

JR Donaubauer, TC McMorris

Index: Donaubauer, John R.; McMorris, Trevor C. Tetrahedron Letters, 1980 , vol. 21, p. 2771 - 2772

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Citation Number: 6

Abstract

Abstract The fungal metabolite lepiochlorin has been synthesized from allylmethoxyethoxymethyl ether and the dianion of 2-phenylthiopropionic acid. The resulting lactone was converted to the butenolide and halogen functions introduced by hydrolysis of the MEM group and treatment with thionyl chloride followed by N-bromosuccinimide. Reaction with silver acetate yielded lepiochlorin.