Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate
Chapter 13, Problem 13.65(choose chapter or problem)
Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting byproduct (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 33903400): OH R HO PBr3 O R 3 dibromide 1 2 + (a) Draw a structure for the desired product (2). (b) Propose a plausible mechanism for formation of byproduct 3 using PBr3 as the reagent. Make sure that your mechanism provides a justification for the stereochemical outcome.
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