143120-75-6Relevant articles and documents
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
, 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.
New asymmetric routes to ajmaline and suaveoline indole alkaloids
Bailey, Patrick D.,Morgan, Keith M.,Smith, David I.,Vernon, John M.
, p. 3566 - 3577 (2007/10/03)
The tetracyclic advanced intermediates 6,8 and 9 obtained from L-tryptophan via a cis-selective Pictet-Spengler reaction and a Dieckmann-Thorpe cyclisation are used in a range of new approaches to polycyclic monoterpenoid indole alkaloids such as ajmaline and suaveoline. Structural modifications designed to facilitate a key intermolecular addition to C15 (ajmaline numbering) are described, followed by two intramolecular routes based on the addition of a suitable carbon fragment to a remote nitrogen atom prior to bond formation at C15. The Royal Society of Chemistry 2000.
The total synthesis of (-)-suaveoline
Bailey, Patrick D.,Morgan, Keith M.
, p. 3578 - 3583 (2007/10/03)
A new synthesis of the indole alkaloid (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described. The Royal Society of Chemistry 2000.
Unusual biomimetic oxidations of indoles: Synthesis of suaveoline and an alkaloid G analogue
Bailey, Patrick D.,Morgan, Keith M.,Rosair, Georgina M.,Thomas, Rhodri Ll.
, p. 8255 - 8259 (2007/10/03)
The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be
A total asymmetric synthesis of (-)-suaveoline
Bailey, Patrick D.,Morgan, Keith M.
, p. 1479 - 1480 (2007/10/03)
A new total synthesis of (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%); key steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons/alkylation procedure, a vinylogous Thorpe cyclization
Pictet-Spengler reactions in aprotic media. The total synthesis of (±) suaveoline
Trudell,Soerens,Weber,Hutchins,Grubisha,Bennett,Cook
, p. 1805 - 1822 (2007/10/02)
The first total synthesis of the indole alkaloid (±)-suaveoline 1 (a macroline-related base and a member of the sarpagine/ajmaline class of alkaloids) was completed in a stereocontrolled fashion. The serial synthesis employed three intramolecular reaction
Total Synthesis of (+/-)-Suaveoline
Trudell, Mark L.,Cook, James M.
, p. 7504 - 7507 (2007/10/02)
The first total synthesis of the indole alkaloid (+/-)-suaveoline (1) (a macroline-related base and a member of the sarpagine/ajmaline class of alkaloids was completed in a stereocontrolled fashion.The serial synthesis employed three intramolecular reacti
