Journal of the American Chemical Society p. 770 - 773 (2016)
Update date:2022-08-03
Topics: Cytotoxic Enantioselective Total synthesis
Veerasamy, Nagarathanam
Ghosh, Ankan
Li, Jinming
Watanabe, Kazuhiro
Serrill, Jeffrey D.
Ishmael, Jane E.
McPhail, Kerry L.
Carter, Rich G.
The total synthesis of mandelalide A and its ring-expanded macrolide isomer isomandelalide A has been achieved. Unexpected high levels of cytotoxicity were observed with the ring-expanded isomandelalide A with a rank order of potency: mandelalide A > isomandelalide A > mandelalide B. Key aspects of the synthesis include Ag-catalyzed cyclizations (AgCC's) to construct both the THF and THP rings present in the macrocycle, diastereoselective Sharpless dihydroylation of a cis-enyne, and lithium acetylide coupling with a chiral epoxide.
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