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Synthesis of the C4-C16 Polyketide Fragment of Portimines A and B.

Xiao-Bo DingHarry R M AitkenEsperanza S PearlDaniel P FurkertMargaret A Brimble
Published in: The Journal of organic chemistry (2021)
Stereoselective synthesis of the C4-C16 polyketide fragment of portimines A and B is reported, enabled by our previously established method for the stereoselective synthesis of syn-α,α'-dihydroxyketones. The preparation of this advanced fragment provides insights useful for the total synthesis of portimines A and B. An asymmetric Evans aldol reaction was used to install the C10-C11 adjacent stereogenic centers before incorporation of indantrione, followed by epoxidation and epoxide opening to forge the challenging syn-α,α'-dihydroxyketone functionality.
Keyphrases
  • molecularly imprinted
  • simultaneous determination
  • solid phase extraction