@article{SchmidtKunzPetersen2012,
  author    = {Schmidt, Bernd and Kunz, Oliver and Petersen, Monib H.},
  title     = {Total syntheses of naturally occurring seimatopolide a and its enantiomer from chiral pool starting materials using a bidirectional strategy},
  series = {The journal of organic chemistry},
  volume    = {77},
  journal   = {The journal of organic chemistry},
  number    = {23},
  publisher = {American Chemical Society},
  address   = {Washington},
  issn      = {0022-3263},
  doi       = {10.1021/jo302359h},
  pages     = {10897 -- 10906},
  year      = {2012},
  abstract  = {Enantioselective total syntheses of both enantiomers of the recently isolated decanolide natural product seimatopolide A are described. The C-2-symmetric building blocks (R,R)-hexa-1,5-diene-3,4-diol (derived from D-mannitol) and its enantiomer (derived from L-(+)-tartrate) serve as key starting materials, which are elaborated in a bidirectional way using a selective mono-cross-metathesis, regio- and stereoselective epoxidation, and regioselective reductive epoxide opening to furnish the first fragment. Both enantiomers of the second fragment, 3-hydroxypent-4-enoic acid, were conveniently obtained through a lipase-catalyzed kinetic resolution and merged with the first fragment via Shiina esterification. An E-selective ring-closing metathesis was used to access the 10-membered lactone. A comparison of the specific optical rotations of synthetic seimatopolides with those reported for the natural product suggests that the originally assigned (3R,6R,7R,9S)-configuration should be corrected to (3S,6S,7S,9R).},
  language  = {en}
}