Related Experiment Videos
Total synthesis of (-)- and (+)-membrenone C
James A Marshall1, Keith C Ellis
1Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA. jam5x@virginia.edu
Organic Letters
|May 9, 2003
Abstract:
[reaction: see text] A synthesis of the polypropionate marine defense substance (+)-membrenone C and its enantiomer that starts from (S)-2-methyl-3-(tert-butyldimethylsilyloxy)propanal is described. Key steps include (1) additions of chiral allenylmetal reagents to effect both chain homologation and the concomitant introduction of four stereo centers, (2) a bis-intramolecular hydrosilylation-oxidation sequence to install beta-hydroxy ketone subunits, and (3) a bis-intramolecular aldol reaction to construct the two dihydropyrone termini.