ja8b01918_si_002.cif (14.95 MB)
Total Synthesis of the Norhasubanan Alkaloid Stephadiamine
dataset
posted on 2018-06-11, 00:00 authored by Nina Hartrampf, Nils Winter, Gabriele Pupo, Brian M. Stoltz, Dirk Trauner(+)-Stephadiamine
is an unusual alkaloid isolated from the vine Stephania
japonica. It features a norhasubanan skeleton,
and contains two adjacent α-tertiary amines, which renders it
an attractive synthetic target. Here, we present the first total synthesis
of stephadiamine, which hinges on an efficient cascade reaction to
implement the aza[4.3.3]propellane core of the alkaloid. The α-aminolactone
moiety in a highly hindered position was installed via Tollens reaction
and Curtius rearrangement. Useful building blocks for the asymmetric
synthesis of morphine and (nor)hasubanan alkaloids are introduced.