Although diazomethane (CH2N2) is often not a useful reagent for preparing cyclopropanes

Chapter 26, Problem 26.34

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Although diazomethane (CH2N2) is often not a useful reagent for preparing cyclopropanes, other diazo compounds give good yields of more complex cyclopropanes. Draw a stepwise mechanism for the conversion of a diazo compound A into B, an intermediate in the synthesis of sirenin, the sperm attractant produced by the female gametes of the water mold Allomyces. CO2CH3 CuI N N CO2CH3 + two steps HO OH diazo compound A B sperm attractant of the female water mold sirenin

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