Nitro-1,7,9-decatriene

Intramolecular Diels-Alder cyclizations of (E)- -nitro-1,7.9-decatrienes under thermal conditions and Lewis acid conditions lead to the formation of decalin ring systems with excellent endo selectivity (Eq. 8.21). This strategy is used for preparing of the AB ring system of norzoanthamine.33... 

D.R. Williams et al. successfully synthesized the AB ring system of norzoanthamine by the intramolecular DIels-Alder cycllzatlon of an ( )-1-nitro-1,7,9-decatriene. The key transformation for establishing the quaternary stereocenter at C12 in the cycloaddition precursor was the Eschenmoser-Clalsen rearrangement. 

Williams, D. R., Brugel, T. A. Intramolecular Diels-Alder Cyclizations of (E)-1-Nitro-1,7,9-decatrienes Synthesis of the AB Ring System of Norzoanthamine. Org. Lett. 2000, 2,1023-1026. 

Nitro-substituted trienes have been demonstrated to be highly reactive IMDA reaction substrates14. ( , ..E )-l-Nitro-l,6,8-decatriene cyclized to give predominantly the trans-fused hexahydro-1 /f-indene. 

Williams, D.R. and Brugel, TA. (2000) Intramolecular Diels-Alder cyclizations of ( )-l-nitro-l,7,9-decatrienes synthesis of the AB ring system of norzoanthamine. Org. Lett., 2, 1023-1026. 

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