130628-22-7Relevant academic research and scientific papers
Synthesis of 13-acylamino-huprines: Different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis
Camps, Pelayo,Gómez, Elena,Mu?oz-Torrero, Diego
, p. 5423 - 5431 (2004)
Two diastereomeric pairs of rationally designed huprines additionally substituted at position 13 with a formamido or an acetamido group have been synthesized as potential high affinity acetylcholinesterase inhibitors. The synthetic sequence involves hydrolysis of two diastereomeric 13-methanesulfonamido-huprines, followed by acylation of the resulting diastereomeric amines. In the hydrolysis reaction, carried out with PPA under harsh conditions, significant amounts of cyclized or rearranged by-products were also formed, depending on the stereochemistry of the starting compound.
