Stereoselective total synthesis of (±)-7-deoxy-trans-dihydronarciclasine, a potent antineoplastic phenanthridone alkaloid

Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives

“…This natural derivative of lycoricidine was first isolated in 1993, and its first enantioselective total synthesis was reported in 1996 . A synthesis of racemic trans ‐dihydrolycoricidine was published in 2009, however, the key strategy employed was similar to Seebach's synthesis of (±)‐1‐desoxy‐2‐lycorinone and McNulty's synthesis of (±)‐2,3‐deoxy‐ trans ‐dihydrolycoricidine (Table ) …”

A Boron‐Based Synthesis of the Natural Product (+)‐trans‐Dihydrolycoricidine

“…In an effort to convert 15 into a derived cyclic lactam, the substrate was subjected to the Banwell‐modified Bischler–Napieralski reaction conditions,18 however, only decomposition products were observed. This problem was remedied by using a strategy similar to that used by Kadas and co‐workers;7b first 15 was subjected to an OsO 4 ‐catalyzed dihydroxylation to afford a single diastereomer of the diol, which was acylated with Ac 2 O. This alternative substrate for the ring closure ( 16 ) was treated with Tf 2 O and DMAP (5:3) to afford the desired lactam 17 in 54 % yield.…”

Hydrogenation of (±)-trans-2-arylnitrocyclohexane derivatives over palladium

“…was supplied by Merck-Schuchardt (Hohenbrunn, Germany). The starting materials (compounds 1a-f) were prepared from the corresponding substituted benzaldehyde derivatives using a four-step synthesis method developed in our laboratory [18]. Their purities, according to GC-MS analyses, were min 99%.…”