Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan
Pages 60-61
The atom-transfer radical reaction has been found quite useful for functionalizing unsaturated organic molecules. The addition of various halocarbons to olefins in the presence of radical initiators is particularly effective for this purpose. Poly-halogenated compounds obtained by this reaction have been used as versatile intermediates for organic synthesis owing to their compatibility with numerous transformations. In the present study, the ACD ring system of paclitaxel (Taxol) has been synthesized from a readily available glucose derivative via radical reactions involving carbon tetrachloride-transfer annulation and photochemical cyclobutanone rearrangement. This synthesis provides a novel route to the chiral ACD ring system that would serve as a key intermediate in the total synthesis of paclitaxel.
