54781-87-2Relevant articles and documents
Govindachari et al.
, p. 891,892,893,896 (1973)
Modular Syntheses of Phenanthroindolizidine Natural Products
Jo, Young-In,Burke, Martin D.,Cheon, Cheol-Hong
, p. 4201 - 4204 (2019/06/14)
A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.
Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization
Liu, Gong-Qing,Reimann, Marcel,Opatz, Till
, p. 6142 - 6148 (2016/07/26)
A concise and modular synthesis of phenanthroindolizidine alkaloids was achieved by combining iodoaminocylization with a free radical cyclization approach. The route described allowed the preparation of (±)-tylophorine, (±)-antofine, and (±)-deoxypergularinine in six steps. When commercially available l-prolinol was used as a chiral building block, (S)-(+)-tylophorine was also synthesized in 49% yield and >99% ee over five linear steps.
Total synthesis of phenanthroindolizidine alkaloids through an amidyl radical cascade/rearrangement reaction
Han, Guifang,Liu, Yuxiu,Wang, Qingmin
, p. 5334 - 5337 (2013/11/06)
A short and general synthesis of the phenanthroindolizidine alkaloids is reported, featuring an unusual amidyl radical 5-exo/5-exo/rearrangement cascade of a xanthate precursor. Second, using an amidyl radical 5-exo/6-endo cascade to synthesize a phenanth