K.C. Nicolaou wrote about his own 1987 synthesis of this compound in the original volume of Classics in Total Synthesis. For 10 points each:
[10h] Name this polyene macrolide, a glycoside produced by Streptomyces that binds to ergosterol to form pores in target cell membranes.
ANSWER: amphotericin B [prompt on amphotericin]
[10e] Nicolaou’s amphotericin B synthesis forms the macrolide ring using the Horner-Wadsworth-Emmons modification of this reaction. This reaction converts carbonyls to alkenes using carbon-phosphorus ylides.
ANSWER: Wittig reaction
[10m] The polyols in the amphotericin ring were synthesized via a series of this reaction. This Nobel-winning reaction is stereoselective because one enantiomer of diethyl tartrate attacks from above the plane of an allylic alcohol, and the other enantiomer attacks from the bottom.
ANSWER: Sharpless epoxidation [or Sharpless asymmetric epoxidation; prompt on epoxidation; prompt on Sharpless; prompt on Sharpless oxidation or oxidation]
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