ol4024997_si_001.pdf (1.63 MB)
Total Synthesis of (−)-18-epi-Peloruside A: An Alkyne Linchpin Strategy
journal contribution
posted on 2016-02-18, 14:58 authored by Barry M. Trost, David J. Michaelis, Sushant MalhotraA 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.
History
Usage metrics
Categories
Keywords
OtherC 18 ethyl stereocentersynthesisMisassignmentdibromoolefinC 18 stereocenterstereochemistryproduct epimericstereodefined enonedioldiastereoselective aldol condensationcytotoxic agent pelorusidedesymmetrization reactionconversionTotal SynthesisAlkyne Linchpin StrategyA convergenthingealkyne linchpin
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC