Total Synthesis of (−)-18-<i>epi</i>-Peloruside A: An Alkyne Linchpin Strategy
Barry M. Trost
David J. Michaelis
Sushant Malhotra
10.1021/ol4024997.s001
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_18_i_epi_i_Peloruside_A_An_Alkyne_Linchpin_Strategy/2365330
A convergent synthetic route toward cytotoxic agent peloruside A that hinges on the use of an alkyne linchpin to assemble the natural product is described. Other highlights of this synthesis include an asymmetric desymmetrization reaction of a 1,3-diol, a one-pot conversion of a dibromoolefin to a stereodefined enone, and a diastereoselective aldol condensation. Misassignment of the absolute stereochemistry of the C18 stereocenter in our synthesis provided the natural product epimeric at the C18 ethyl stereocenter.
2016-02-18 14:58:34
Other
C 18 ethyl stereocenter
synthesis
Misassignment
dibromoolefin
C 18 stereocenter
stereochemistry
product epimeric
stereodefined enone
diol
diastereoselective aldol condensation
cytotoxic agent peloruside
desymmetrization reaction
conversion
Total Synthesis
Alkyne Linchpin StrategyA convergent
hinge
alkyne linchpin