473742-41-5Relevant articles and documents
Total synthesis of (-)- and enf-(+)-vindorosine: Tandem intramolecular -diels-alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles
Elliott, Gregory I.,Velcicky, Juraj,Ishikawa, Hayato,Li, YongKai,Boger, Dale L.
, p. 620 - 622 (2007/10/03)
(Chemical Equation Presented) From tandem to pentacycle: The intramolecular tandem [4+2]/[3+2] cycloaddicycloaddition cascade of 1,3,4-oxadiazole (Z)-1 to give the pentacyclic skeleton 2 of (-)- and ent-(+)-vindorosine introduces all the requisite substituents and functionality in a single step by which three new rings and four C-C bonds form and all six key stereocenters are installed.
Total synthesis of (-)- and ent-(+)-vindoline
Choi, Younggi,Ishikawa, Hayato,Velcicky, Juraj,Elliott, Gregory I.,Miller, Michael M.,Boger, Dale L.
, p. 4539 - 4542 (2007/10/03)
(Chemical Equation Presented) Two exceptionally concise total syntheses of (-)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C-C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.
