Synthesis (and alternative proof of configuration) of the scyphostatin C(1')-C(20') trienoyl fragment.
[reaction--see text] Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the recently reported (Org. Lett. 2000, 2, 505) stereochemical assignment. A strategy for the stereoselective synthesis of 2 has been achieved.
Hoye
T R
TR
Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
Tennakoon
M A
MA
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D011753:Pyrones; C121123:scyphostatin