106356-50-7Relevant academic research and scientific papers
A New Efficient Total Synthesis of Vindorosine and Vindoline
Andriamialisoa, Ratremaniaina Zo,Langlois, Nicole,Langlois, Yves
, p. 961 - 967 (1985)
Highly stereoselective total syntheses of indole alkaloids vindorosine (1a) and vindoline (1b) are described.An imino Diels-Alder reaction, a stereospecific alkylation, and a rearrangement induced by the Pummerer reaction are the key steps of these short and high overall yield sequences.
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).
Biomimetic Alkaloid Syntheses. 15. Enantioselective Syntheses with Epichlorohydrin: Total Syntheses of (+)-, (-)-, and (+/-)-Vindoline and a Synthesis of (-)-Vindorosine
Kuehne, Martin E.,Podhorez, David E.,Mulamba, Tshilundu,Bornmann, William G.
, p. 347 - 353 (2007/10/02)
Total syntheses of vindoline (1) in racemic as well as in each enantiomeric form and of (-)-vindorosine (2) are described.They were achieved by generation and diastereoselective cyclizations of 14-hydroxysecodine intermediates 6 and 7.The subsequent oxidative elaboration of ring E was also studied with 3-oxotabersonine (24), 3-oxovincadifformine (26), and 14β-hydroxyvincadifformine (15).Na-Methyltabersonine (22) was oxidized to a ring-D-contracted α-keto lactam, 23.
