Tetrahedron Letters p. 4143 - 4146 (1998)
Update date:2022-08-23
Topics:
Urrutia, Anahi
Rodriguez, J. Gonzalo
The natural cis[ABCD] tetracycle of the 20-methyl analogue of aspidospermidine has been synthesised, starting from the 4,4-ethylenedioxy- 1-cyclohexanone. This, was transformed into 3-methyl-3-(3'-nitropropyl)- 1,2,3,4-tetrahydrocarbazol-4-one. Two key synthetic steps permits the construction of the D ring: i) the one pot nickel boride catalyst to the imine tetracycle in excellent yield; and ii) the stereoselective reduction of this imine to the natural cis D ring junction in good yield.
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