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Total synthesis of mycalamide A and 7-epi-mycalamide A
1Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu
Organic Letters
|February 7, 2001
Abstract:
[formula: see text] The final stages of a total synthesis of mycalamide A are described. A key step is the aldol reaction (mismatched) of imide 4 and aldehyde 5 which provided a ca. 5:4 mixture of aldols 10a and 10b, with incorrect C(7) stereochemistry. Elaboration of the 10a-10b mixture to mycalamide A required epimerization of C(7) at the stage of beta-keto imide 11. Alternatively, Swern oxidation of the 10a-10b mixture under conditions that minimize C(7) epimerization led to 7-epi-mycalamide A selectively.