Total syntheses of (+)-paspalicine and (+)-paspalinine

• DOI: 10.1021/ja00178a071
• Publication Date: 2005-03-18T23:15:13Z
• Authors: Amos B. Smith; Toshiaki Sunazuka; Tamara L. Leenay; Jill Kingery-Wood
• Keywords: 01 natural sciences; 0104 chemical sciences

The cornerstone of the approach comprised a stereocontrolled, nine-step construction of tricyclic ketone (−)-5 [9.4% overall yield from (+)-Wieland-Miescher ketone], a prospective common intermediate containing the critical C(12b,12c) vicinal quaternary centers. In this communication we demonstrate the viability of this unified strategy with the first total syntheses of (+)-paspalicine (2) and (+)-paspalinine (3)