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The compound fusarisetin A (isolated from a soil fungus) displays significant anticancer
Chapter 22, Problem 22.118(choose chapter or problem)
The compound fusarisetin A (isolated from a soil fungus) displays significant anticancer activity without detectable cytotoxicity (toxicity to cells). A key step in a reported synthesis of the enantiomer of fusarisetin A involves a Dieckmann cyclization followed by the intramolecular formation of a hemiacetal under basic conditions (J. Am. Chem. Soc. 2012, 134, 920923). Provide a mechanism consistent with this transformation. H H OH H H O N O O OMe OH H H H H O O N O OH OH NaOMe
Questions & Answers
QUESTION:
The compound fusarisetin A (isolated from a soil fungus) displays significant anticancer activity without detectable cytotoxicity (toxicity to cells). A key step in a reported synthesis of the enantiomer of fusarisetin A involves a Dieckmann cyclization followed by the intramolecular formation of a hemiacetal under basic conditions (J. Am. Chem. Soc. 2012, 134, 920923). Provide a mechanism consistent with this transformation. H H OH H H O N O O OMe OH H H H H O O N O OH OH NaOMe
ANSWER:Problem 22.118The compound fusarisetin A (isolated from a soil fungus) displays significant anticanceractivity without detectable cytotoxicity (toxicity to cells). A key step in a reported synthesisof the enantiomer of fusarisetin A involves a Dieckmann cyclization followed by theintramolecular formation of a hemiacetal under basic conditions (J. Am. Chem. Soc. 2012,134, 920923). Provide a mechanism consistent with this transformation. H H OH H H O NO O OMe OH H H H H O O N O OH OH NaOMe. Step by step solutionStep 1 of 3The compound fusarisetin A contains an active acidic proton due to the presence of twocarbonyl groups.NaOMe is a base and it accepts a proton from an acidic position and forms enolate as shownbelow.______________________________________________________________________________\n