217448-31-2Relevant academic research and scientific papers
Total synthesis of suaveoline and norsuaveoline via intramolecular oxazole-olefin Diels-Alder reaction
Ohba, Masashi,Natsutani, Itaru,Sakuma, Takashi
, p. 6471 - 6474 (2004)
Total synthesis of two Rauwolfia alkaloids, suaveoline (1) and norsuaveoline (2), has been achieved through a highly stereoselective route starting from l-tryptophan methyl ester (9) and exploiting the intramolecular Diels-Alder reaction of the oxazole-ol
Facile Synthesis of Pyridines from Propargyl Amines: Concise Total Synthesis of Suaveoline Alkaloids
Zhao, Zhiwen,Wei, Hongbo,Xiao, Ke,Cheng, Bin,Zhai, Hongbin,Li, Yun
supporting information, p. 1148 - 1152 (2019/01/04)
A general and efficient protocol was developed for the synthesis of polysubstituted pyridines from propargyl amines and unsaturated carbonyl compounds through a tandem condensation/alkyne isomerization/6π 3-azatriene electrocyclization sequence. This process was found to be applicable to a wide range of readily available substrates (30 examples, up to 95 % yield) and could be readily performed on a preparative (20 g) scale. By taking advantage of this method for late-stage pyridine incorporation, we successfully completed the collective total synthesis of suveoline, norsuveoline, and macrophylline.
Quick Access to Pyridines through 6π-3-Azatriene Electrocyclization: Concise Total Synthesis of Suaveoline Alkaloids
Li, Yun,Wei, Hongbo
, p. 1615 - 1620 (2019/08/26)
Pyridine is a prevalent structural heterocyclic motifs in natural products, pharmaceuticals, and advanced materials. Several different methodologies have been developed for the synthesis of these kinds of molecules. However, a sustainable and efficient procedure for the synthesis of pyridines is still highly desirable. In this Synpacts article, we highlight our recent approach to the construction of highly substituted pyridines though a tandem condensation/alkyne isomerization/6π-3-azatriene electrocyclization sequence. The present protocol was used to synthesize a series of polysubstituted pyridines (30 examples) in moderate to good yields. The process also permitted the development of a concise strategy for collective total syntheses of suaveoline, norsuaveoline, and macrophylline.
Intramolecular Diels-Alder reactions of oxazole-olefins: synthesis of the Rauwolfia alkaloids suaveoline and norsuaveoline
Ohba, Masashi,Natsutani, Itaru,Sakuma, Takashi
, p. 10337 - 10344 (2008/02/13)
A full account of the highly stereoselective total synthesis of two indole alkaloids, suaveoline (4) and norsuaveoline (5), is presented. Central features of the synthetic strategy include the conversion of l-tryptophan methyl ester (12) into the oxazole
General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction
Li, Jin,Wang, Tao,Yu, Peng,Peterson,Weber,Soerens,Grubisha,Bennett,Cook
, p. 6998 - 7010 (2007/10/03)
A general approach (oxyanion-Cope strategy) for the synthesis of sarpagine/ajmaline indole alkaloids has been developed. (+)-Ajmaline 1 and alkaloid G 2 as well as norsuaveoline 3 have been synthesized from D-(+)-tryptophan in enantiospecific fashion via
The enantiospecific total synthesis of norsuaveoline
Wang, Tao,Yu, Peng,Li, Jin,Cook, James M.
, p. 8009 - 8012 (2007/10/03)
Norsuaveoline la has been synthesized enantiospecifically in 28% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled oxy-anion Cope rearrangement as key steps.
