206359-55-9Relevant academic research and scientific papers
Asymmetric syntheses of panclicins A-E via [2+2] cycloaddition of alkyl(trimethylsilyl)ketenes to a β-silyloxyaldehyde
Kocienski, Philip J.,Pelotier, Beatrice,Pons, Jean-Marc,Prideaux, Heather
, p. 1373 - 1382 (1998)
Panclicins A-E, pancreatic lipase inhibitors from Streptomyces, were synthesised in a modular fashion starting with three alkyl(trimethylsilyl)ketenes, two amino acids and a single aldehyde component, (3R)-3-(tert-butyldimethylsilyloxy)decanal 11. The lone stereocentre in 11 which governs the stereochemistry in subsequent steps was generated by Noyori asymmetric hydrogenation. The key step, a Lewis acid catalysed [2+2] cycloaddition of alkyl(trimethylsilyl)ketenes 13a-c to 11, gave three 3-trimethylsilyloxetan-2-ones with good 1,3-asymmetric induction. After C- and O-desilylation the amino acid side chains were introduced using a Mitsunobu inversion.
