77101-58-7Relevant academic research and scientific papers
A New Indole Alkaloid, 14α-Hydroxyrauniticine: Structure Revision and Partial Synthesis
Yamanaka, Etsuji,Maruta, Etsuko,Kasamatsu, Satoe,Aimi, Norio,Sakai, Shin-ichiro,et. al.
, p. 3713 - 3721 (2007/10/02)
Oxidation of the enamine (6) with dibenzoyl peroxide followed by reduction with NaBH4 gave the benzoate (8), which was converted to the cis-hydroxyl compound (9), while hydroboration-oxidation of 6 gave the trans-isomer (11).Treatment of a mixture of the enamines (13 and 14) with dibenzoyl peroxide/NaBH4 gave the benzoates (15 and 16), which were converted to 14α-hydroxy-3-isorauniticine (17) and the acetal (18), respectively.Hydroboration-oxidation of 13 gave 14α-hydroxyrauniticine (2), which was found to be identical with the natural alkaloid whose structure had erroneously been proposed as 14β-hydroxy-3-isorauniticine (4).Keywords-indole alkaloid; 14α-hydroxyrauniticine; structure revision; partial synthesis; Uncaria attenuata; enamine; hydroxylation; hydroboration
INTRODUCTION OF HYDROXYL GROUP AT C-14 OF INDOLE ALKALOIDS: THE PARTIAL SYNTHESIS OF 14α-HYDROXYRAUNITICINE
Yamanaka, Etsuji,Maruta, Etsuko,Kasamatsu, Satoe,Aimi, Norio,Sakai, Shin-ichiro,et al.
, p. 3861 - 3864 (2007/10/02)
Stereoselective hydroxylation at C-1 of the indoloquinolizidine (1) to the hydroxyl derivatives (5 and 6) and the partial synthesis of 14α-hydroxyrauniticine (11) from rauniticine (7) are described.
