Total synthesis of clavaminol A, C and H.

نویسندگان

  • Ahmed M Zaed
  • Andrew Sutherland
چکیده

The first total synthesis of clavaminol A and C, (2R,3S)-2-amino-3-alkanols from the Mediterranean ascidian Clavelina phlegraea has been achieved in 29% overall yield. The key step involved a palladium(II)-catalysed directed Overman rearrangement to create the C-N bond and install the erythro configuration while a one-pot, tributyltin hydride-mediated reduction allowed simultaneous formation of the methyl side-chain and N-acetyl group. Similarly, the first total synthesis of clavaminol H was completed in 48% overall yield using an approach that also provided the cytotoxic des-acetyl analogue.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 9 23  شماره 

صفحات  -

تاریخ انتشار 2011