F. J. Leeper and P. Padmanabhan
"Stereospecific Nucleophilic Ring-Opening of a Deuteriated Cyclopropylcarbinol"
Tetrahedron Lett.,1989, 30, 5017-5020. Full Text
The stereospecifically deuteriated phenyl cyclopropyl carbinol (3b) was synthesized from chiral alcohol (8). Ring-opening to the homoallylic alcohol (4) was shown to proceed with clean inversion of configuration by 1H n.m.r. spectroscopy of the ring-opened product with a chiral shift reagent. The indolizidine alkaloid (1) can be degraded to (3) and this will provide a method to analyse the stereochemistry of its biosynthesis.
Department of Chemistry
University of Cambridge