1063170-05-7Relevant academic research and scientific papers
Total synthesis of (+)-trans-dihydronarciclasine by a catalytic enantioselective regiodivergent nitroso Diels-Alder reaction
Jana, Chandan Kumar,Studer, Armido
supporting information; experimental part, p. 6326 - 6328 (2009/06/28)
A method was proposed to demonstrate the total synthesis of (+)-trans-dihydronarciclasine by a catalytic enantioselective regiodivergent nitroso Diels-Alder reaction. The study used enantioselective introso Diels-Alder reaction for the transformation of racemic dienes to the adducts. The study found that ring closure can occur by a Bischler-Napieralski reaction or by lactamization. The Br-Li exchange and transmetalation to copper with Fe-complexed cyclohexadienyl cation and oxidative decomplexation can provide diene in 85% yield. The study observed that the pyridyl group was cleaved by quarternizing the pyridyl moiety with methyl triflate and hydrolysis of the pyridinium salt. The study also observed that the biologically active natural products can be prepared in large amount by using this method.
