title: Total synthesis of clavaminol A, C and H.
abstract: 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.
authors: WestCHEM, School of Chemistry, University of Glasgow, Glasgow, UK G12 8QQ.
authors: Ahmed M
authors: AM
authors: Zaed
authors: Andrew
authors: A
authors: Sutherland
mesh_terms: D002518:Ceramides / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D002518:Ceramides; C569126:clavaminol A; C569127:clavaminol C; C553735:clavaminol H