Nodulisporic acid side-chain modifications: access to the 2", 3", 4", and 6" registers.

@article{Chakravarty2003NodulisporicAS,
  title={Nodulisporic acid side-chain modifications: access to the 2", 3", 4", and 6" registers.},
  author={Prasun K Chakravarty and Thomas Shih and Steven L Colletti and Michelle B Ayer and Christine Snedden and Howard Kuo and Sriram Tyagarajan and Lynn Gregory and Michelle Zakson-Aiken and Wesley L Shoop and Dennis M Schmatz and MatthewJ Wyvratt and Michael Hallsworth Greg Fisher and Peter T. Meinke},
  journal={Bioorganic & medicinal chemistry letters},
  year={2003},
  volume={13 1},
  pages={147-50}
}
Efficient routes to access the 2", 3", 4", and 6" registers of the nodulisporic acid (NsA) side chain are disclosed. A mild one-carbon, Ph(2)CdoublebondNCH(2)CtriplebondN mediated homologation of NsA's 3"-aldehyde permitted access to the 4"-register. Curtius reaction of NsA's 3"-acid yielded the corresponding 2"-aldehyde 4 from which the unnatural Delta(2",3")-olefin isomer 2b was obtained. In addition, Arndt-Eistert reactions of the parent NsA permitted a one-carbon homologation to the 6… CONTINUE READING

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