DEAD 0. The crude 9. The reaction mixture was concentrated and the ane—EtOAc, affording pure threo-6 mg, 1. The chloroacetate was hydrolyzed using K2CO3 threo-6 mg, 2. The MeOH was evaporated [a]D20 —22 c 1. To a solution of threo-6 mg, 1.
The mixture was then filtered through Celite, and After 10 min, the reaction was quenched with sat. The solids were washed with CH2Cl2 6. Evaporation at reduced pres- 2. The spectroscopic data Synthesis , No. After an additional tion mixture was allowed to warm to r. After stirring for 40 min, 30 min, hexanes 5. The residue was The residue was purified by flash chromatography to provide 11; diluted with EtOAc 5.
Further purification was not done at this stage; [a]D20 — Compound 9 90 mg, 0. Then, sat. The com- The mixture was washed with sat. The crude amine 12 11 mg, 0. To the mixture was added in the follow- ing order: DME 0. The reaction mixture was 1. The resulting mixture was diluted with CHCl3 4. The After 20 min, the reaction was quenched with sat. Na2SO4 0. Evaporation at reduced pres- found: The scientific literature contains many reports on the isolation and synthesis.
The first racemic total synthesis of lupinine occurred in by Clemo, Morgan, and Raper. Abstract To date, more than congeners of the akuammiline alkaloid family have been isolated. Their signature structural element Lupinine - an overview ScienceDirect Topics. Two alternative protocols. Lupinine - the chemical stopping you from eating Lupin — University. Risi, Andrew M. Maza, and Steven D. The Journal of Organic Chemistry , 80 1 , Sergey V. Tsukanov and Daniel L. Total Synthesis of Alkaloid B. The Journal of Organic Chemistry , 79 19 , Morris, and Jon S.
Organic Letters , 15 21 , Journal of Natural Products , 76 4 , Applied Hydroformylation. Chemical Reviews , 11 , The Journal of Organic Chemistry , 77 18 , Organic Letters , 14 7 , Organic Letters , 13 23 , Organic Letters , 13 16 , Tarun K.
Pradhan, K. Organic Letters , 13 7 , Alan R. Benzotriazolyl-sulfonyl Azide for Diazotransfer and Preparation of Azidoacylbenzotriazoles. The Journal of Organic Chemistry , 75 19 , Tetrahedron , 73 52 , Asian Journal of Organic Chemistry , 6 5 , Joseph P. Simple Indolizidine and Quinolizidine Alkaloids.Tetrahedron , 65, Detailed experimental procedures and spectral and analytical data for all the compounds. Angewandte Chemie International Edition , 51 10 ,
After stirring for 40 min, 30 min, hexanes 5. Scheme 4 Synthesis of — -equiquinamide 2 zwitterion and hydrochloride salt. Fletcher, Paul M. Lupanine and Sparteine, two prominent members of the tetracyclic.
This route provides enantiomerically pure 1- stereoselectivity of the reaction was significantly affected azabicyclo[4. Tetrahedron Letters , 54 8 , Andrade, C. Further purification was not done at this stage; [a]D20 — Tetrahedron , 73 52 , Fuentes, and Matthew L.
Garraffo, H. This compound was prepared following the experimental procedure according to reference 3c; mp The Journal of Organic Chemistry , 75 19 , Gary M. Chemistry - A European Journal , 18 4 ,