2912-26-7Relevant articles and documents
Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation
Antropow, Alyssa H.,Garcia, Nicholas R.,White, Kolby L.,Movassaghi, Mohammad
supporting information, p. 3647 - 3650 (2018/06/26)
The first enantioselective total synthesis of (-)-vallesine via a strategy that features a late-stage regioselective C17-oxidation followed by a highly stereoselective transannular cyclization is reported. The versatility of this approach is highlighted by the divergent synthesis of the archetypal alkaloid of this family, (+)-aspidospermidine, and an A-ring-oxygenated derivative, (+)-deacetylaspidospermine, the precursor to (-)-vallesine, from a common intermediate.
Total synthesis of (-)-aspidospermine via diastereoselective ring-closing olefin metathesis
Fukuda, Yu-Ichi,Shindo, Mitsuru,Shishido, Kozo
, p. 749 - 751 (2007/10/03)
(Matrix presented) An enantiocontrolled total synthesis of (-)-aspidospermine has been achieved. The key element of the strategy is the diastereoselective construction of the quaternary stereogenic center employing 1,4-asymmetric induction during the ring-closing olefin metathesis.