Synthesis of model BC bicycles of taxol using C10–C11 ring-closing metathesis strategy

Model BC ring-systems of taxol 23b and 28b, which lack an oxygenated substituent at C7, have been efficiently synthesized. The key step is a ring-closing metathesis (RCM) to form the 8-membered B ring between C10 and C11. Comparison of the metathesis reaction in this route with the RCM used in a previous study with similar substrates is highlighted.

Graphical abstractModel BC ring-systems of taxol have been synthesized by ring-closing metathesis (RCM). The influence of the stereochemistry and the protecting groups of the diol moiety on the formation of the eight-membered ring has been studied. Comparison with the RCM used on similar substrates in a previous route is presented.Figure optionsDownload full-size imageDownload as PowerPoint slide