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Sphingolipids are a class of compounds that play an important role in signal transmission and cell recognition. Fumonisin B1 is a potent sphingolipid biosynthesis inhibitor.

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Sphingolipids are a class of compounds that play an important role in signal transmission and cell recognition. Fumonisin B1 is a potent sphingolipid biosynthesis inhibitor. A recent synthesis of fumonisin B1 employed the transformation shown below. The carbon atoms numbered 7-9 are incorporated into the carbon skeleton via the formation of alkyne 2 from epoxide 1 (Tetrahedron Lett. 2012, 53, 3233-3236). Starting with 3-bromo-1-propyne, show a synthesis of alkyne 2 from epoxide 1. This transformation can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. AH3O+workupBMgCtBuOK D NaNH2H2, Lindlar's cat. epoxide 1

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