113541-83-6Relevant academic research and scientific papers
Phosphoric acid catalyzed desymmetrization of bicyclic bislactones bearing an all-carbon stereogenic center: Total syntheses of (-)-rhazinilam and (-)-leucomidine B
Gualtierotti, Jean-Baptiste,Pasche, Delphine,Wang, Qian,Zhu, Jieping
, p. 9926 - 9930,5 (2014)
In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcohols took place smoothly to afford enantiomerically enriched monoacids having an all-carbon stereogenic center. Concise catalytic enantioselective syntheses of both (-)-rhazinilam and (-)-leucomidine B were subsequently developed using (S)-methyl 4-ethyl-4-formylpimelate monoacid as a common starting material. Breaking symmetry: Achiral bislactones (1) undergo desymmetrization by reaction with alcohol in the presence of chiral imidodiphosphoric acids. The monoacids 2, having an all-carbon stereogenic center, were obtained in good to excellent yields and enantioselectivities. Concise total syntheses of (-)-rhazinilam and (-)-leucomidine B were subsequently developed using 2 as a common starting material.
ION-RADICAL PROMOTED CYCLIZATION OF A δ,ε-VINYLIMINE: THE TOTAL SYNTHESIS OF (+/-)-TUBOXENINE
Cartier, Dominique,Ouahrani, Mohammed,Hugel, Georgette,Levy, Jean
, p. 657 - 662 (2007/10/02)
3-Oxo-1,2,18,19-tetradehydroaspidospermidine 8b was synthesized by a modification of a previous synthesis of vincadifformine 10.It was cyclized (Na/THF) to 3-oxotuboxenine 22, which was reduced with LiAlH4 to (+/-)-tuboxenine (1).
APPROACHES TO THE SYNTHESIS OF ASPIDOSPERMA ALKALOIDS. PART II. THE SYNTHESIS OF 18,19-DIDEHYDROTABERSONINE.
Blowers, John W.,Saxton, J. Edwin,Swanson, Alistair G.
, p. 6071 - 6095 (2007/10/02)
The total synthesis of 18,19-dehydrotabersonine, via 3-oxo-18,19-didehydrovincadifformine, is described.
