473742-40-4Relevant articles and documents
Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids
Ishikawa, Hayato,Elliott, Gregory I.,Velcicky, Juraj,Choi, Younggi,Boger, Dale L.
, p. 10596 - 10612 (2007/10/03)
A concise 11-step total synthesis of (-)- and ent-(+)-vindoline (3) is detailed based on a unique tandem intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which three rings and four C-C bonds are formed central to the characteristic pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. As key elements of the scope and stereochemical features of the reaction were defined, a series of related natural products of increasing complexity were prepared by total synthesis including both enantiomers of minovine (4), 4-desacetoxy-6,7-dihydrovindorosine (5), 4-desacetoxyvindorosine (6), and vindorosine (7) as well as /V-methylaspidospermidine (11). Subsequent extensions of the approach provided both enantiomers of 6,7-dihydrovindoline (8), 4-desacetoxyvindoline (9), and 4-desacetoxy-6,7-dihydrovindoline (10).
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.
