Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 23, Pages 8030-8037Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06060k
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- Libyan People's Bureau, London
- University of Glasgow
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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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