Synthesis of 6,6-dimethyltricyclo[5.4.0.02,8]undecane-2,9-diol for (ent-)longipinane-type sesquiterpenoids using two types of radical cyclization reactions

Add time:08/28/2019    Source:sciencedirect.com

A synthetic route to 6,6-dimethyltricyclo[5.4.0.02,8]undecane-2,9-diol, a key precursor to (ent-)longipinane-type sesquiterpenoids, is described. This unique core common to (ent-)longipinanes was constructed using two types of intramolecular radical cyclization reactions, namely, intramolecular coupling of an acid chloride and an alkyl iodide mediated by SmI2, TBAI and HMPA, and the coupling of a ketone and an epoxide mediated by Cp2TiI2 and SmI2.

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