245648-24-2Relevant academic research and scientific papers
Vinylogous Mannich reactions. Stereoselective formal synthesis of pumiliotoxin 251D
Martin, Stephen F.,Bur, Scott K.
, p. 8905 - 8914 (2007/10/03)
A concise synthesis of (-)-3, a known precursor of pumiliotoxin 251D, has been completed using a vinylogous Mannich reaction as a key construction. Silyloxyfuran 10 added to methoxypyrrolidine 20 in the presence of TMS-OTf to give a mixture (4.8:1) of 21 and 22 in 57% yield. Reduction and global deprotection of 21 afforded the bicyclic lactam 23. Raney Nickel mediated extrusion of the hydroxymethyl group from 23 gave (-)-3.
