Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 122, Issue 8, Pages 1658-1663Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja993598n
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Mn(III)-mediated oxidative free radical cyclization reactions are useful for construction of polycyclic compounds. In the total synthesis of triptolide (3) and its related compounds, construction of tricyclic skeletons 4 and 5 was achieved by the Mn(OAc)(3)-mediated oxidative radical cyclization of a series of acyclic precursors 6-9. The addition of a catalytic amount of lanthanide triflates was found to significantly improve the rate and stereoselectivity of those radical cyclization reactions. The effects of the benzylic oxygen substituents and alpha-substituents (chloro and methyl) on the radical cyclization reactions were also investigated. Transition-state models were proposed to explain the observed stereoselectivity.
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