574-99-2Relevant academic research and scientific papers
Short total synthesis of (-)-lupinine and (-)-epiquinamide by double Mitsunobu reaction
Santos, Leonardo Silva,Mirabal-Gallardo, Yaneris,Shankaraiah, Nagula,Simirgiotis, Mario J.
, p. 51 - 56 (2011/02/26)
Alternative total syntheses of (-)-lupinine (1) and (-)-epiquinamide (2) have been described via the key intermediate 3 obtained from the addition of 2-trialkylsilyloxyfuran 5 to N-acyliminium intermediate derived from 4. The major R,R-isomer 8 obtained from the Mannich reaction was converted into its R,S-isomer through Mitsunobu reaction. Then, a second Mitsunobu reaction of 3 led to cyano 9 and azido 11 derivatives, which were converted into 1 and 2 in 33 and 36% overall yield from 4, respectively. The synthetic route is amenable for the generation of several quinolizidine alkaloids. Georg Thieme Verlag Stuttgart · New York.
