92803-94-6Relevant academic research and scientific papers
Studies in Terpenoid Biosynthesis. Part 39. The Stereochemistry of the Relationship Between Substrate and Oxidant in the Hydroxylation of Aphidicolin at C-18 by Cephalosporium aphidicola
Hanson, James R.,Hitchcock, Peter B.,Jarvis, Andrew G.,Ratcliffe, Arnold H.
, p. 2079 - 2085 (2007/10/02)
The preparation of some 3α,18-oxetane analogues of intermediates in the biosynthesis of aphidicolin is described.Their stereoselective labelling at C-18 with deuterium is reported.Biotransformation studies using these substrates with Cephalosporium aphidicola have shown that the 18-pro-R-hydrogen is removed in hydroxylation at this centre suggesting a Re stereochemical relationship between the substrate and oxidant for the normal hydroxylation at C-18.The X-ray crystallographic structure of 3α,18-oxetane 6 is presented and compared with that of aphidicolin 17-nor-16-ketone 13.
