Four steps in the synthesis of helminthosporal, a toxin produced by a wheat plant
Chapter 24, Problem 24.67(choose chapter or problem)
Four steps in the synthesis of helminthosporal, a toxin produced by a wheat plant fungus, are shown below. O O + O O CHO CHO helminthosporal OHC O CHO NaOEt, EtOH HCO2Et H3O+ O O [1] [2] [4] [3] a. What compounds are needed to carry out Step [1]? b. What compounds are needed to carry out Step [2]? c. Write a detailed mechanism for Step [3]. d. Write a detailed mechanism for Step [4]. What is unusual about the product of this reaction? e. Step [1] adds a formyl group (HCO ) and Step [3] removes it. Why was this apparently unnecessary process done?
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