618458-14-3Relevant academic research and scientific papers
A spontaneous bicyclization facilitates a synthesis of (-)-hispidospermidin
Tamiya, Junko,Sorensen, Erik J.
, p. 6921 - 6932 (2007/10/03)
A concise, enantiospecific synthesis of the phospholipase C inhibitor (-)-hispidospermidin (1) has been achieved by approximating the architecture of a reactive intermediate that may lie on the biosynthetic pathway leading to this natural product. Two compounds derived from (R)-(+)-pulegone were joined by a highly diastereoselective carbonyl addition. A proximity-facilitated, acid-induced bicyclization of spiro[4.5]deca-1,7-diene 29 gave rise to the tetracyclic framework of 1 and was the key transformation in this synthesis.
